乙二胺与对甲基苯酚的Mannich反应
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摘要
Mannich碱型Salen配体是重要的立体化学模型,在过渡金属配位化合物中占有重要的的地位。本文运用Mannich反应合成了一系列的新型Salen配体,配体化合物通过核磁、红外、质谱、元素分析进行了表征,并通过X-射线单晶衍射仪确定了三个配体的晶体结构。本文首先由乙二胺、对甲酚和多聚甲醛以不同的摩尔比在无溶剂的条件下合成了三种Mannich碱。其次利用乙二胺衍生物的Mannich反应在无催化剂的条件下设计合成了11种Salen型新的配体,在Salen配体中引入呋喃杂环,对其与金属的配位提供了多种可能性。
1.在无溶剂的条件下采用一步法合成了两种新型化合物,N, N, N', N'-四(2-羟基-5-甲苄基)乙二胺和N, N, N'-三(2-羟基-5-甲苄基)乙二胺,采用无溶剂的方法符合绿色化学的理念,反应采用“一锅煮”,既简化了操作,也有效地提高了产率,确立了每一种结构的最优的反应配比。
2.化合物3 (N, N'-二(2-羟基-5-甲苄基)乙二胺)不易从反应体系中析出,采取将其转化为盐酸盐的形式,能较容易的从反应体系中析出,可以得到较纯的产物。在相似的条件下,将对甲酚改为对叔丁基苯酚、对甲氧基苯酚、对氯苯酚,得到了类似的三种Mannich碱。
3.将化合物N, N, N', N'-四(2-羟基-5-甲苄基)乙二胺,N, N, N'-三(2-羟基-5-甲苄基)乙二胺在N, N-二甲基甲酰胺和乙醚的混合溶剂中,在自然挥发的条件下得到了两种无色透明的晶体,经单晶X-射线衍射分析确认其结构。
4.通过Mannich反应,以乙二胺苯甲醛席夫碱和乙二胺呋喃甲醛席夫碱采用硼氢化钠还原为二元仲胺,以此作为碱组分,与甲醛、多种对取代苯酚生成了11种Salen型新的配体。研究了酚的种类对Mannich碱的影响,当2, 4-二取代苯酚,如2, 4-二甲基苯酚、2, 4-二叔丁基苯酚、2, 4-二氯苯酚与二元仲胺反应时,产率较高,而且较容易从反应体系中析出。当酚为对取代苯酚时,则产物需在深冷的条件下才能从反应体系中析出。当苯环上连有叔丁基时,相对于其他苯酚,产率也较高。
5.通过缩合的方法制备了酚醛树脂型高分子的Mannich碱,采用核磁、元素分析以及激光光散射对酚醛树脂型高分子型Mannich碱的结构进行了表征,结果表明,测试结果与理论相符合。
Salen coordination compounds is important in the field of transition metal coordination chemistry and stereochemistry . In this thesis, eleven coordination complexes were synthesized by Mannich condensation. The chemical structures of the title compounds were characterized by elementary analysis, IR, 1H NMR and MS spectroscopic data. Three compounds were identified by single crystal X-ray diffraction analysis. Three kinds Mannich base were synthesized by ethylenediamine, p-cresol and the paraformaldehyde in different ratio under no solvent condensation. Eleven kinds Mannich base were kinds were synthesized with benzene rings or furan rings. Salen ligands with furan rings which could provide coordination modes to metal ions.
1. N, N, N'-Tri(2-hydroxy-5-methoxylbenzyl)ethanediamine and N, N, N', N'- tetrakis (2-hydroxyl-5-methoxylbenzyl)ethanediamine were synthesized under solvent-free conditions, A novel one pot and solvent-free become one of the hotspots of green chemistry.
2. N, N'-Bis(2-hydroxy-5-methoxylbenzyl)ethanediamine is difficult separate from the mixtures, it can translate relevant hydrochloride after acidification of the reaction mixture to pH 1-2 with concentrated hydrochloric acid, Target product can recrystallization from ethanol after the hydrochloride was added into sodium carbonate.
3. N, N, N'-Tri(2-hydroxy-5-methoxylbenzyl)ethanediamine and N, N, N' N'-Tetrakis (2-hydroxyl-5-methoxylbenzyl)ethanediamine were used to obtain single crystals suitable for X-ray diffraction studies, the crystal structure and properties were characterized and studied.
4. Eleven kinds Mannich base were synthesized by the reduzate of Schiff bases of ethylenediamine with benzaldehyde, or ethylenediamine with furaldehyde and paraformaldehyde, substitute phenol without catalyst. The substituent species and the position on phenyl ring effects the reaction.
5. Liner macromolecule mannich base was synthesized by N, N'-Bis(2- hydroxy-5-methoxylbenzyl)ethanediamine and formaldehyde in acid catalysis, the structure was determined by 1H NMR。
1.在无溶剂的条件下采用一步法合成了两种新型化合物,N, N, N', N'-四(2-羟基-5-甲苄基)乙二胺和N, N, N'-三(2-羟基-5-甲苄基)乙二胺,采用无溶剂的方法符合绿色化学的理念,反应采用“一锅煮”,既简化了操作,也有效地提高了产率,确立了每一种结构的最优的反应配比。
2.化合物3 (N, N'-二(2-羟基-5-甲苄基)乙二胺)不易从反应体系中析出,采取将其转化为盐酸盐的形式,能较容易的从反应体系中析出,可以得到较纯的产物。在相似的条件下,将对甲酚改为对叔丁基苯酚、对甲氧基苯酚、对氯苯酚,得到了类似的三种Mannich碱。
3.将化合物N, N, N', N'-四(2-羟基-5-甲苄基)乙二胺,N, N, N'-三(2-羟基-5-甲苄基)乙二胺在N, N-二甲基甲酰胺和乙醚的混合溶剂中,在自然挥发的条件下得到了两种无色透明的晶体,经单晶X-射线衍射分析确认其结构。
4.通过Mannich反应,以乙二胺苯甲醛席夫碱和乙二胺呋喃甲醛席夫碱采用硼氢化钠还原为二元仲胺,以此作为碱组分,与甲醛、多种对取代苯酚生成了11种Salen型新的配体。研究了酚的种类对Mannich碱的影响,当2, 4-二取代苯酚,如2, 4-二甲基苯酚、2, 4-二叔丁基苯酚、2, 4-二氯苯酚与二元仲胺反应时,产率较高,而且较容易从反应体系中析出。当酚为对取代苯酚时,则产物需在深冷的条件下才能从反应体系中析出。当苯环上连有叔丁基时,相对于其他苯酚,产率也较高。
5.通过缩合的方法制备了酚醛树脂型高分子的Mannich碱,采用核磁、元素分析以及激光光散射对酚醛树脂型高分子型Mannich碱的结构进行了表征,结果表明,测试结果与理论相符合。
Salen coordination compounds is important in the field of transition metal coordination chemistry and stereochemistry . In this thesis, eleven coordination complexes were synthesized by Mannich condensation. The chemical structures of the title compounds were characterized by elementary analysis, IR, 1H NMR and MS spectroscopic data. Three compounds were identified by single crystal X-ray diffraction analysis. Three kinds Mannich base were synthesized by ethylenediamine, p-cresol and the paraformaldehyde in different ratio under no solvent condensation. Eleven kinds Mannich base were kinds were synthesized with benzene rings or furan rings. Salen ligands with furan rings which could provide coordination modes to metal ions.
1. N, N, N'-Tri(2-hydroxy-5-methoxylbenzyl)ethanediamine and N, N, N', N'- tetrakis (2-hydroxyl-5-methoxylbenzyl)ethanediamine were synthesized under solvent-free conditions, A novel one pot and solvent-free become one of the hotspots of green chemistry.
2. N, N'-Bis(2-hydroxy-5-methoxylbenzyl)ethanediamine is difficult separate from the mixtures, it can translate relevant hydrochloride after acidification of the reaction mixture to pH 1-2 with concentrated hydrochloric acid, Target product can recrystallization from ethanol after the hydrochloride was added into sodium carbonate.
3. N, N, N'-Tri(2-hydroxy-5-methoxylbenzyl)ethanediamine and N, N, N' N'-Tetrakis (2-hydroxyl-5-methoxylbenzyl)ethanediamine were used to obtain single crystals suitable for X-ray diffraction studies, the crystal structure and properties were characterized and studied.
4. Eleven kinds Mannich base were synthesized by the reduzate of Schiff bases of ethylenediamine with benzaldehyde, or ethylenediamine with furaldehyde and paraformaldehyde, substitute phenol without catalyst. The substituent species and the position on phenyl ring effects the reaction.
5. Liner macromolecule mannich base was synthesized by N, N'-Bis(2- hydroxy-5-methoxylbenzyl)ethanediamine and formaldehyde in acid catalysis, the structure was determined by 1H NMR。
引文
[1]万道正.曼尼希反应和曼尼希碱化学[M]北京:科学出版社, 1986.
[2] Ashok M., Holla B. S., Poojary B. Convenient one pot synthesis and antimicrobial evaluation of some new Mannich bases carrying 4-methylthiobenzyl moiety[J]. European Journal of Medicinal Chemistry, 2007 42(8): 1095-1101.
[3] Vinkovic V., Sunjic V. A highly stereocontrolled synthesis of (S)-(-)-3- (4-tert-butyl)phenyl-1-N-(cis-2,6-dimethyl)morpholinyl-2-methylpropane via asymmetric Mannich reaction[J] Tetrahedron, 1997, 53(2): 689-696.
[4] Bandgar B. P., Patil S. A., Korbad B. L., Biradar S. C., Nile S. N., Khobragade C. N. Synthesis and biological evaluation of a novel series of 2,2- bisaminomethylated aurone analogs as anti-inflammatory and antimicrobial agents[J]. European Journal of Medicinal Chemistry, 2010, 45(7): 3223-3227.
[5] Tramontini M.Futher advances in the chemistry of Mannich bases[J]. Tetrahedron, 1990, 46: 1791-1837.
[6] Michael A., Bernhard W., Nikolaus R., Modern variants of the Mannich Reaction[J]. Angewandte Chemie International Edition, 1998, 37: 1045-1070.
[7] Singh A., Wahi A. K. Synthesis, characterization and antimicrobial activity of some new Mannich bases derived from 4-amino triazoles[J] Research Journal of Pharmaceutical, Biological and Chemical Sciences, 2011, 2(2): 896-903.
[8] Vijayraghavan S., Somani R. R., Shirodkar P. Y., Kadam V. J., Synthesis and antimicrobial activity of some newer Mannich bases[J], Indian Journal of Heterocyclic Chemistry 2008, 18(2): 137-140.
[9] Schmid M. B., Zeitler, K., Gschwind R. M. NMR Investigations on the Proline-Catalyzed Aldehyde Self-Condensation: Mannich Mechanism, Dienamine Detection, and Erosion of the Aldol Addition Selectivity[J]. Journal of Organic Chemistry, 2011, 76(9): 3005-3015.
[10] Kocsis B., Kustos I., Kilar F., Nyul A., Jakus P. B., Kerekes S., Villarreal V., Prokai L., Lorand T. Antifungal unsaturated cyclic Mannich ketones and amino alcohols: Study of mechanism of action[J]. European Journal of Medicinal Chemistry, 2009, 44(5): 1823-1829.
[11] Zhao Q. Y., Shi M. Axially chiral phosphine-oxazoline ligands in silver(I)-catalyzed asymmetric Mannich reaction of N-Boc aldimines with trimethylsiloxyfuran[J]. Tetrahedron, 2011, 67(20): 3724-3732.
[12] Szatmari I., Fulop F. Solvent-free synthesis of 1-(hydroxyquinolyl)- and 1-(hydroxyisoquinolyl)-1,2,3,4-tetrahydroisoquinolines by modified mannich reaction[J]. Synthesis, 2011, 5: 745-748.
[13] Krishnan G. R., Sreekumar K. Three component Mannich reaction and 1,5-benzodiazepine synthesis catalyzed by a tetranitrile-silver complex[J]. Letters in Organic Chemistry, 2009, 6(1): 17-21.
[14] Cummings T. F., Shelton J. R. Mannich reaction mechanisms[J]. Journal of Organic Chemistry, 1960, 25: 419-423.
[15] Mauro M., Erika N., Mariangela M., Alessandro B., Marco F., Maurizio F., Marco t. M., Sabrina P., Paolo L. C., Fabio M., Cristina I., Roberta L., Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae[J]. Bioorganic & Medicinal Chemistry, 2008, 16: 2591-2605.
[16] Yujiro H.,Tatsuya U., Seiji A., Tsubasa O.,Kazaki O. Organic Solvent-Free,Enantio and Diastereoselective,Direct Mannich Reaction in the Presence of water[J]. Organic Letters ., 2008, 10(1): 21-24.
[17]陈光旭,徐秀娟,赵冬.芳香胺参加的Mannich反应.芳香胺与苄叉丙酮的Mannich反应[J].化学学报, 1986, 44: 846-849.
[18]门秀琴.过渡金属催化下有机卤化锌试剂与芳醛和芳胺的反应研究[D].甘肃:西北师范大学,2004.
[19]肖鹤鸣,唐泽华,高宝华.可多重N-羟甲基化的Mannich反应机理研究[J].化学学报, 1986. 12: 56-59.
[20] Davoodnia, A., Tavakoli-N. A., Tavakoli-Hoseini, N. Carbon-based solid acid - catalyzed one-pot Mannich reaction. A facile synthesis of -amino carbonyl compounds[J]. Bulletin of the Korean Chemical Society, 2011, 32(2): 635-638.
[21] Yue C. B. Aromatic Compounds Mannich Reaction Using Economical Acidic Ionic Liquids Based on Morpholinium Salts as Dual Solvent- Catalysts[J] Synthetic Communications, 2010, 40(24): 3640-3647.
[22] Gerald F. G., Raymond I. B.J. The Mannich Reaction Involving Optically Active Substituted Mandelic Acids and Nitroalkanes[J]. Journal of the American Chemical Society, 1951, 73, 5598-5560.
[23] Thomas A. B., Gordon H. B., Curtis J. R., Richard E. D. Performed Mannich salts:a facile preparation of dimethyl(methylene)anunonium iodide[J]. Journal of Organic Chemistry[J]. 1980,45(3):524-525.
[24] Caldwell H. C., Nobles W. L. Mannich bases from 5-nitro-2-acetylfuran and 5-nitro-2-furfuralacetone[J]. Journal of the American Pharmaceutical Association,1955, 44(5): 273-275
[25] Alexander E. R., Underhill, E. J. The mechanism of the Mannich reaction. I. Ethylmalonic acid, a methynyl compound[J] Journal of the American Chemical Society, 1949, 71: 4014-4019.
[26] Presello J. S., Subramanian R. Graft copolymerization of polyacrylamide-based cationic water-soluble polymers[J]. Polymer, 2007, 48(2): 184-185.
[27] Xia J., Qiu R. h., Yin S. F., Zhang X. W., Luo S. l., Xia K., Wong, W. Y. Synthesis and structure of an air-stable organoantimony complex and its use as a catalyst for direct diastereoselective Mannich reactions in water[J]. Journal of Organometallic Chemistry, 2010, 695(10-11): 1487-1492.
[28] Sharghi H., Khalifeh R., Beni A. R. Synthesis of new lariat ethers containing polycyclic phenols and heterocyclic aromatic compound on graphite surface via Mannich reaction[J] Journal of the Iranian Chemical Society, 2010, 7(1): 275-288.
[29] Matsumura Y., Ikeda, T., Onomura O. The Mannich -type reaction between N,O-acetals and carbon nucleophiles under solvent-free conditions[J]. Heterocycles, 2006, 67(1): 113-117.
[30] Nielsen S. V., Pedersen E. B. Phosphorus pentoxide in organic synthesis. XXIX. Synthesis of 4-arylamino-5, 6, 7, 8-tetrahydro -1H- pyrazolo [3,4-b] quinolines and the corresponding N- Mannich bases[J]. Liebigs Annalen der Chemie 1986 (10): 1728-1735.
[31] Sharghi H., Sakineh E. A convenient and efficient method for the preparation of unique fluorophores of lariat naphtho-aza-crown ethers[J] Helvetica Chimica Acta, 2008, 91(7): 1363-1373.
[32] Sahoo S.; Joseph T.; Halligudi S. B. Mannich reaction in Broensted acidic ionic liquid: A facile synthesis of -amino carbonyl compounds[J]. Journal of Molecular Catalysis A: Chemical, 2006, 244(1-2): 179-182.
[33]德国专利DRP:89979;90907.
[34] Zhu L. P., Fang L. Y., Zhang Y., Chen H. P., He D. H., Chen M. C., Xu, K. Catalytic thioalkylation of phenols based on Mannich -type phenol[J]. Synthetic Communications, 2007, 37(15): 2609-2613.
[35] Rondot C., Zhu J. P. Synthesis of Chiral Vicinal Diamines by Highly Diastereoselective Three-Component Phenolic Mannich Reaction: Temperature- Dependent Stereodivergency[J] Organic Letters, 2005, 7(8), 1641- 1644.
[36] Gerald B. R., Zhang H. L., Rowland E. B., Spandan C., Yong w., Jon C.Antilla.Bronsted Acid~Catalyzed Imine Amidation[J]. Journal of the American Chemical Society, 2005, 127(45): 1569-15697.
[37] Moehrle H., Miller C., Wendisch D. Mannich bases. VIII. Structure of products from the Betti reaction with ammonia[J]. Chemische Berichte, 1974, 107(8): 2675-2682.
[38] Kumar A., Gupta M. K., Kumar M. Non-ionic surfactant catalyzed synthesis of Betti base in water[J]. Tetrahedron Letters, 2010, 51(12):1582-1584.
[39]恽魁宏等.有机化学[M].天津:高等教育出版社,1983,370-371.
[40]刘祖广,陈朝晖,王迪珍.木质素的Mannich反应研究进展[J]中国造纸学报, 2007, 22(1):104-107.
[41]张万烽,林青,林健,汤建军,陆姗. Mannich法合成木质素胺型沥青乳化剂及其分析[J]应用化工, 2006, 35(5):366-370.
[42] Donald G. R., Charles H. L. Lignin composition and process for its prepration[P]. US: 3912706, 1975.
[43] Bakirova, I. N., Zenitova L. A., Rozental N. A. Effect of acetylacetone on the reaction of polyethylene glycol adipate with diisocyanate in the presence of phenolic Mannich bases and properties of castable polyurethanes[J] Russian Journal of Applied Chemistry, 2006, 79(5): 811-813.
[44] Lonoscu M,Mihai S,Roibu C and Preoteasa V.New aromatic mannich polyols[J].Polyurethanes expo 2003, 1: 641-642
[45] Thomas F. C., Sheltion J, R. Mannich Reaction Mechanisms[J]. The Journal of Organic Chemistry, 2002, 25(3): 419-423.
[46] Worrel C. J., Detroit, M. Gasoline additive concentrate composition[P]. US: 3994698, 1976.
[47] Kobayashi H. I.Catalytic enantioselective addition to imines[J] Chemical Reviews, 1999, 99(5): 1069-1072.
[48] Andrew E. T., Ahmed M.α-Imino esters: versatile substrates for the catalytic, asymmetric synthesis ofα-andβ-amino acids andβ-lactams[J]. Accounts of Chemical Research, 2003, 36: 10.
[49] Bilgic O., Young D. W., A general and practicable synthesis of polycyclic heteroaromatic compounds. Part 3. Extension of the synthesis to quinone methides of naphthalene, phenanthrene, and benzene[J] Journal of the Chemical Society, 1980, (6): 1233-1239.
[50] Laetitia C., David C. S. Utilisation of homogeneous and supported chiral metal(Salen) complexes in asymmetric catalysis[J]. Chemical Society Reviews,1999, 28: 85-93.
[51] He B., Chen F. X., Li Y., Feng, X. M., Zhang, G. L. Effective activation of the chiral Salen /Ti(OiPr)4 catalyst with achiral phenolic N-oxides as additives in the enantioselective cyanosilylation of ketones[J]. European Journal of Organic Chemistry, 2004, (22): 4657-4666.
[52] Sasmita M., Suresh D., Maravanji S., Balakrishna J. An inexpensive and highly stable ligand 1,4-bis(2-hydroxy-3,5-ditert-butylbenzyl) piperazine for Mizoroki- Heck and room temperature Suzuki-Miyaura CROSS-coupling reactions[J]. Tetrahedron, 2008, 64:240-247.
[53]任晓光,周继敏,宋永吉,於晖.曼尼希碱复合缓蚀剂的缓蚀性能研究[J]石油化工腐蚀与防护, 2010, 5:123-127.
[54]陈刚,杨乃旺,汤颖,张黎,张洁.木质素磺酸盐Mannich碱钻井液处理剂的合成与性能研究[J]钻井液与完井液, 2010, 27(4):13-15.
[55] Chen D., Zhai X., Yuan Q. H., Luo J., Xie S. C., Gong P. Synthesis and in vitro anti-hepatitis B virus activity of 1H-benzimidazol-5-ol derivatives[J] Chinese Chemical Letters. 2010, 21(11): 1326-1329.
[56] Shaw A. Y., Chang, C. Y., Hsu M. Y., Lu P. J., Yang C. N., Chen H. L., Lo C.W., Shiau C. W., Chern M. K. Synthesis and structure-activity relationship study of 8-hydroxyquinoline-derived Mannich bases as anticancer agents[J]. European Journal of Medicinal Chemistry, 2010, 45(7):2860-2867.
[57] Chantarasiri N, Ruangpornvisuti V, Muangsin N, Structure and physico-chemical properties of hexadentate Schiff base zinc complexes derived from salicylaldehydes and triethylenetetramine[J] Journal of Molecular Structure, 2004, 701 (1): 93-103.
[58]张英菊,吕小兵.环己二胺手性席夫碱配体的合成与表征[J]合成化学, 2005, 13(1): 64-66.
[59] SUN Y, TANG N. Enantioselective epoxidation of olefins catalyzed by chiral dimeric and partially water-soluble monomeric Salen-Mn(III) complexes in the presence of novel co-catalysts[J].J. Mol. Catal. A: Chem., 2006, 255 (1): 171-179.
[60] MOBIAN P., KERN J. M., SAUVAGE J. P. Catenane Constructed around a Ru(Diimine)32+ complex used as a template[J] J. Am. Chem. Sol., 2003, 125 (2): 2016-2017.
[61] Ma H., Chen S. H., Studies on Electrochemical Behavior of Copper in Aerated NaBr Solutions with Schiff Base[J]. J. Electrochem. Soc., 2001, 148 (5): 208-216.
[62] Mizuno T., Yamamoto M., Takeuchi M., Sugar chirality sensing using a prochiral Salen-Co(II) complex[J]. Tetrahedron, 2000, 56 (34): 6193-6198.
[63]李连生,吴琉林.手性(Salen)Co在不对称催化反应和天然产物合成中的应用[J].有机化学, 2000, 20(5): 689-700.
[64] Shldon R. A., Koehi J. K., Metal catalysed oxidations of organic compounds [M]. New York: Academic Press. 1981, 97: 102-105.
[65] Ding L. Q., Chu Z., Chen L. L., Lue X. Q., Yan B., Song J. R., Fan D. D., Bao F. Pd- Salen and Pd-Salan complexes: Characterization and application in styrene polymerization[J]. Inorganic Chemistry Communications, 2011, 14(4), 573-577.
[66] Kemper S., Hrobarik P., Kaupp M., Schloerer N. E. Jacobsen's Catalyst for Hydrolytic Kinetic Resolution: Structure Elucidation of Paramagnetic Co(III) Salen Complexes in Solution via Combined NMR and Quantum Chemical Studies. Journal of the American Chemical Society, 2009, 131(12), 4172-4173.
[67] Huhta, T. A., Farrell J. R., Multidentate aminophenol ligands synthesized using Mannich condensations. Abstracts of Papers, 241st ACS National Meeting United States, March, 2011, 27-31.
[68] Abdul-Ghani, A. J., Al-Jeboori, M, J., Al-Karawi A. J. M. Synthesis and spectral studies of new N2S2 and N2O2 Mannich base ligands and their metal complexes. Journal of Coordination Chemistry, 2009, 62(16): 2736-2744.
[69] Maurya M. R., Khurana S. R. D. Six-coordinated oxovanadium(V) complexes of reduced Schiff bases derived from amino acids: synthesis, reactivity and redox studies[J]. Transition Metal Chemistry, 2003, 28(5):511-517.
[70] Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution, University of G?ttingen, Germany 1990.
[71] Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement, University of G?ttingen, Germany 1997.
[72] Dai H. F., Chen C. H., Chen C. S., Yeh W. Y. Synthesis and Characterization of the Triple Cluster (Cp3Fe4(CO)4(C5H4CH=NCH2CH2))3N and Its Function as a Tripodal Tetradentate[J] Ligand Organometallics[J] 2011, 30(10): 2889-2892.
[73] Musa M. A. Khan M. O., Aspedon A., Cooperwood J. S. Synthesis and antimicrobial activity of N, N'– Bis (2-hydroxylbenzyl) - 1, 2 - ethanediamine derivatives[J]. Letters in Drug Design & Discovery 2010, 7(3): 165-170.
[74] Luo H. T., Kang Y., Li Q., Yang L. M. Sulfamic acid as efficient and reusable catalytic system for the synthesis of pyrrole, furan, and thiophene derivatives[J]. Heteroatom Chemistry, 2008, 19(2): 144-148.
[75] Previtera T., Vigorita M. G., Basile M., Fenech, G., Trovato A., Occhiuto F., Monforte M. T., Barbera R., 3,3'-Di(1,3-thiazolidin-4-one) system. V. Synthesisand pharmacological properties of 3,3'(1,2-ethanediyl)bis(2-heteroaryl-1, 3-thiazolidin-4- one) derivatives[J]. European Journal of Medicinal Chemistry 1990, 25(7): 569-579.
[76]张雄,蔡丽华,黄丽芬,朱静静.糠醛双Schiff碱及其铜配合物的合成与抗菌活性研究[J]化学与生物工程, 2010, 27(4): 152-155.
[77] Lanznaster M.; Neves A., Bortoluzzi, A. J., Assumpcao A. M. C., Vencato I., Machado, S. P., Drechsel S. M. Electronic Effects of Electron-Donating and -Withdrawing Groups in Model Complexes for Iron-Tyrosine-Containing Metalloenzymes[J]. Inorganic Chemistry, 2006, 45(3): 1005-1011.
[78] Rajasekar M., Sreedaran S., Prabu R., Narayanan V., Jegadeesh R., Raaman N., Rahiman A. K. Synthesis, characterization, and antimicrobial activities of nickel(II) and copper(II) Schiff-base complexes[J]. Journal of Coordination Chemistry, 2010, 63(1): 136-146.
[79] Wang W., Zhang F. X., Li J., Zhang R. L. New complex of manganese(II) with Schiff base derived from furaldehyde and diethylenetriamine[J]. Russian Journal of Coordination Chemistry, 2010, 36(5): 378-380.
[80] Ali M. A., Bose R. N. Transition metal complexes of furfural and benzil Schiff bases derived from S-benzyldithiocarbazate[J]. Polyhedron, 1984, 3(5): 517-522.
[81] Tudisco C., Sfrazzetto G. T., Pappalardo A., Motta A., Tomaselli G. A., Fragala I. L., Ballistreri F. P., Condorelli G. G. Covalent Functionalization of Silicon Surfaces with a Cavitand- Modified Salen[J]. European Journal of Inorganic Chemistry, 2011, (13): 2124-2131.
[82] Yun X., Hu X. B, Jin Z., Hu J., Yan C.; Yao J., Li H. Copper- Salen catalysts modified by ionic compounds for the oxidation of cyclohexene by oxygen[J]. Journal of Molecular Catalysis A: Chemical, 2010, 327(1-2): 25-31.
[83]王英,徐小平,姚英明,纪顺俊. 1,2二[3-(6-甲基-8-叔丁基-3,4-二氢-1,3苯并噁嗪)基]乙烷与新型双氮桥联四酚化合物的合成[J].合成化学,2010, 18(6): 715-717.
[84] Diego S. A., Hugo K., Rodrigo R., Ramiro A., Fernando G., Maria T. G. Fuentealba Heterobimetallic RePd complexes bridged byη~1:η~5-Ph_2PC_5_H_4 ligand. Synthesis, electronic and crystal structure of (CO)2(PR_3)(η_5-C_5H_4PPh_2)Re–PdCl_2, R = Me and Ome[J] Dalton Trans., 2010,39: 6295-6301.
[85] Al-Gharabli S. I., Ebraheem K. A. K., Mubarak M. S. Synthesis and chelation properties of a new copper selective Mannich polymer containing a 2,4-dihydroxybenzaldoxime group[J]. Journal of Saudi Chemical Society, 2001, 5(3): 399-406.
[86] Park S.; Piyachaturawat P., Taylor A. E., Huang C. Potential N-nitrosodimethy -lamine (NDMA) formation from amine-based water treatment polymers in the reactions with chlorine-based oxidants and nitrosifying agents[J]. Water Science & Technology: Water Supply, 2009, 9(3), 279-288.
[87] Stark J. L., Johnson K. B. Additive useful for stabilizing fuel oils.[P] WO 2009046192
[88]徐秀娟,陈光旭.用酮作为酸组分的Mannich碱的合成[J].有机化学,1985, 4, 284-296.
[89]黎刚,祁健,杨芳,刘荣,张松梅.以哌嗪做连接的壬基酚聚氧乙烯醚三聚表面活性剂[P]. 200910069618.2
[90]徐晶.高分子席夫碱的合成与应用[D].大连轻工业学院,大连:2006
[91] Kais A. K. E., Mohammad S. M., Samer I. A. Synthesis And Chelation Properties Of Some New Mannich Condensation Polymers Containing A Salicylaldoxime Group[J]. Journal of Macromolecular Science: Pure and Applied Chemistry, 2002, 39: 217-229.
[2] Ashok M., Holla B. S., Poojary B. Convenient one pot synthesis and antimicrobial evaluation of some new Mannich bases carrying 4-methylthiobenzyl moiety[J]. European Journal of Medicinal Chemistry, 2007 42(8): 1095-1101.
[3] Vinkovic V., Sunjic V. A highly stereocontrolled synthesis of (S)-(-)-3- (4-tert-butyl)phenyl-1-N-(cis-2,6-dimethyl)morpholinyl-2-methylpropane via asymmetric Mannich reaction[J] Tetrahedron, 1997, 53(2): 689-696.
[4] Bandgar B. P., Patil S. A., Korbad B. L., Biradar S. C., Nile S. N., Khobragade C. N. Synthesis and biological evaluation of a novel series of 2,2- bisaminomethylated aurone analogs as anti-inflammatory and antimicrobial agents[J]. European Journal of Medicinal Chemistry, 2010, 45(7): 3223-3227.
[5] Tramontini M.Futher advances in the chemistry of Mannich bases[J]. Tetrahedron, 1990, 46: 1791-1837.
[6] Michael A., Bernhard W., Nikolaus R., Modern variants of the Mannich Reaction[J]. Angewandte Chemie International Edition, 1998, 37: 1045-1070.
[7] Singh A., Wahi A. K. Synthesis, characterization and antimicrobial activity of some new Mannich bases derived from 4-amino triazoles[J] Research Journal of Pharmaceutical, Biological and Chemical Sciences, 2011, 2(2): 896-903.
[8] Vijayraghavan S., Somani R. R., Shirodkar P. Y., Kadam V. J., Synthesis and antimicrobial activity of some newer Mannich bases[J], Indian Journal of Heterocyclic Chemistry 2008, 18(2): 137-140.
[9] Schmid M. B., Zeitler, K., Gschwind R. M. NMR Investigations on the Proline-Catalyzed Aldehyde Self-Condensation: Mannich Mechanism, Dienamine Detection, and Erosion of the Aldol Addition Selectivity[J]. Journal of Organic Chemistry, 2011, 76(9): 3005-3015.
[10] Kocsis B., Kustos I., Kilar F., Nyul A., Jakus P. B., Kerekes S., Villarreal V., Prokai L., Lorand T. Antifungal unsaturated cyclic Mannich ketones and amino alcohols: Study of mechanism of action[J]. European Journal of Medicinal Chemistry, 2009, 44(5): 1823-1829.
[11] Zhao Q. Y., Shi M. Axially chiral phosphine-oxazoline ligands in silver(I)-catalyzed asymmetric Mannich reaction of N-Boc aldimines with trimethylsiloxyfuran[J]. Tetrahedron, 2011, 67(20): 3724-3732.
[12] Szatmari I., Fulop F. Solvent-free synthesis of 1-(hydroxyquinolyl)- and 1-(hydroxyisoquinolyl)-1,2,3,4-tetrahydroisoquinolines by modified mannich reaction[J]. Synthesis, 2011, 5: 745-748.
[13] Krishnan G. R., Sreekumar K. Three component Mannich reaction and 1,5-benzodiazepine synthesis catalyzed by a tetranitrile-silver complex[J]. Letters in Organic Chemistry, 2009, 6(1): 17-21.
[14] Cummings T. F., Shelton J. R. Mannich reaction mechanisms[J]. Journal of Organic Chemistry, 1960, 25: 419-423.
[15] Mauro M., Erika N., Mariangela M., Alessandro B., Marco F., Maurizio F., Marco t. M., Sabrina P., Paolo L. C., Fabio M., Cristina I., Roberta L., Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae[J]. Bioorganic & Medicinal Chemistry, 2008, 16: 2591-2605.
[16] Yujiro H.,Tatsuya U., Seiji A., Tsubasa O.,Kazaki O. Organic Solvent-Free,Enantio and Diastereoselective,Direct Mannich Reaction in the Presence of water[J]. Organic Letters ., 2008, 10(1): 21-24.
[17]陈光旭,徐秀娟,赵冬.芳香胺参加的Mannich反应.芳香胺与苄叉丙酮的Mannich反应[J].化学学报, 1986, 44: 846-849.
[18]门秀琴.过渡金属催化下有机卤化锌试剂与芳醛和芳胺的反应研究[D].甘肃:西北师范大学,2004.
[19]肖鹤鸣,唐泽华,高宝华.可多重N-羟甲基化的Mannich反应机理研究[J].化学学报, 1986. 12: 56-59.
[20] Davoodnia, A., Tavakoli-N. A., Tavakoli-Hoseini, N. Carbon-based solid acid - catalyzed one-pot Mannich reaction. A facile synthesis of -amino carbonyl compounds[J]. Bulletin of the Korean Chemical Society, 2011, 32(2): 635-638.
[21] Yue C. B. Aromatic Compounds Mannich Reaction Using Economical Acidic Ionic Liquids Based on Morpholinium Salts as Dual Solvent- Catalysts[J] Synthetic Communications, 2010, 40(24): 3640-3647.
[22] Gerald F. G., Raymond I. B.J. The Mannich Reaction Involving Optically Active Substituted Mandelic Acids and Nitroalkanes[J]. Journal of the American Chemical Society, 1951, 73, 5598-5560.
[23] Thomas A. B., Gordon H. B., Curtis J. R., Richard E. D. Performed Mannich salts:a facile preparation of dimethyl(methylene)anunonium iodide[J]. Journal of Organic Chemistry[J]. 1980,45(3):524-525.
[24] Caldwell H. C., Nobles W. L. Mannich bases from 5-nitro-2-acetylfuran and 5-nitro-2-furfuralacetone[J]. Journal of the American Pharmaceutical Association,1955, 44(5): 273-275
[25] Alexander E. R., Underhill, E. J. The mechanism of the Mannich reaction. I. Ethylmalonic acid, a methynyl compound[J] Journal of the American Chemical Society, 1949, 71: 4014-4019.
[26] Presello J. S., Subramanian R. Graft copolymerization of polyacrylamide-based cationic water-soluble polymers[J]. Polymer, 2007, 48(2): 184-185.
[27] Xia J., Qiu R. h., Yin S. F., Zhang X. W., Luo S. l., Xia K., Wong, W. Y. Synthesis and structure of an air-stable organoantimony complex and its use as a catalyst for direct diastereoselective Mannich reactions in water[J]. Journal of Organometallic Chemistry, 2010, 695(10-11): 1487-1492.
[28] Sharghi H., Khalifeh R., Beni A. R. Synthesis of new lariat ethers containing polycyclic phenols and heterocyclic aromatic compound on graphite surface via Mannich reaction[J] Journal of the Iranian Chemical Society, 2010, 7(1): 275-288.
[29] Matsumura Y., Ikeda, T., Onomura O. The Mannich -type reaction between N,O-acetals and carbon nucleophiles under solvent-free conditions[J]. Heterocycles, 2006, 67(1): 113-117.
[30] Nielsen S. V., Pedersen E. B. Phosphorus pentoxide in organic synthesis. XXIX. Synthesis of 4-arylamino-5, 6, 7, 8-tetrahydro -1H- pyrazolo [3,4-b] quinolines and the corresponding N- Mannich bases[J]. Liebigs Annalen der Chemie 1986 (10): 1728-1735.
[31] Sharghi H., Sakineh E. A convenient and efficient method for the preparation of unique fluorophores of lariat naphtho-aza-crown ethers[J] Helvetica Chimica Acta, 2008, 91(7): 1363-1373.
[32] Sahoo S.; Joseph T.; Halligudi S. B. Mannich reaction in Broensted acidic ionic liquid: A facile synthesis of -amino carbonyl compounds[J]. Journal of Molecular Catalysis A: Chemical, 2006, 244(1-2): 179-182.
[33]德国专利DRP:89979;90907.
[34] Zhu L. P., Fang L. Y., Zhang Y., Chen H. P., He D. H., Chen M. C., Xu, K. Catalytic thioalkylation of phenols based on Mannich -type phenol[J]. Synthetic Communications, 2007, 37(15): 2609-2613.
[35] Rondot C., Zhu J. P. Synthesis of Chiral Vicinal Diamines by Highly Diastereoselective Three-Component Phenolic Mannich Reaction: Temperature- Dependent Stereodivergency[J] Organic Letters, 2005, 7(8), 1641- 1644.
[36] Gerald B. R., Zhang H. L., Rowland E. B., Spandan C., Yong w., Jon C.Antilla.Bronsted Acid~Catalyzed Imine Amidation[J]. Journal of the American Chemical Society, 2005, 127(45): 1569-15697.
[37] Moehrle H., Miller C., Wendisch D. Mannich bases. VIII. Structure of products from the Betti reaction with ammonia[J]. Chemische Berichte, 1974, 107(8): 2675-2682.
[38] Kumar A., Gupta M. K., Kumar M. Non-ionic surfactant catalyzed synthesis of Betti base in water[J]. Tetrahedron Letters, 2010, 51(12):1582-1584.
[39]恽魁宏等.有机化学[M].天津:高等教育出版社,1983,370-371.
[40]刘祖广,陈朝晖,王迪珍.木质素的Mannich反应研究进展[J]中国造纸学报, 2007, 22(1):104-107.
[41]张万烽,林青,林健,汤建军,陆姗. Mannich法合成木质素胺型沥青乳化剂及其分析[J]应用化工, 2006, 35(5):366-370.
[42] Donald G. R., Charles H. L. Lignin composition and process for its prepration[P]. US: 3912706, 1975.
[43] Bakirova, I. N., Zenitova L. A., Rozental N. A. Effect of acetylacetone on the reaction of polyethylene glycol adipate with diisocyanate in the presence of phenolic Mannich bases and properties of castable polyurethanes[J] Russian Journal of Applied Chemistry, 2006, 79(5): 811-813.
[44] Lonoscu M,Mihai S,Roibu C and Preoteasa V.New aromatic mannich polyols[J].Polyurethanes expo 2003, 1: 641-642
[45] Thomas F. C., Sheltion J, R. Mannich Reaction Mechanisms[J]. The Journal of Organic Chemistry, 2002, 25(3): 419-423.
[46] Worrel C. J., Detroit, M. Gasoline additive concentrate composition[P]. US: 3994698, 1976.
[47] Kobayashi H. I.Catalytic enantioselective addition to imines[J] Chemical Reviews, 1999, 99(5): 1069-1072.
[48] Andrew E. T., Ahmed M.α-Imino esters: versatile substrates for the catalytic, asymmetric synthesis ofα-andβ-amino acids andβ-lactams[J]. Accounts of Chemical Research, 2003, 36: 10.
[49] Bilgic O., Young D. W., A general and practicable synthesis of polycyclic heteroaromatic compounds. Part 3. Extension of the synthesis to quinone methides of naphthalene, phenanthrene, and benzene[J] Journal of the Chemical Society, 1980, (6): 1233-1239.
[50] Laetitia C., David C. S. Utilisation of homogeneous and supported chiral metal(Salen) complexes in asymmetric catalysis[J]. Chemical Society Reviews,1999, 28: 85-93.
[51] He B., Chen F. X., Li Y., Feng, X. M., Zhang, G. L. Effective activation of the chiral Salen /Ti(OiPr)4 catalyst with achiral phenolic N-oxides as additives in the enantioselective cyanosilylation of ketones[J]. European Journal of Organic Chemistry, 2004, (22): 4657-4666.
[52] Sasmita M., Suresh D., Maravanji S., Balakrishna J. An inexpensive and highly stable ligand 1,4-bis(2-hydroxy-3,5-ditert-butylbenzyl) piperazine for Mizoroki- Heck and room temperature Suzuki-Miyaura CROSS-coupling reactions[J]. Tetrahedron, 2008, 64:240-247.
[53]任晓光,周继敏,宋永吉,於晖.曼尼希碱复合缓蚀剂的缓蚀性能研究[J]石油化工腐蚀与防护, 2010, 5:123-127.
[54]陈刚,杨乃旺,汤颖,张黎,张洁.木质素磺酸盐Mannich碱钻井液处理剂的合成与性能研究[J]钻井液与完井液, 2010, 27(4):13-15.
[55] Chen D., Zhai X., Yuan Q. H., Luo J., Xie S. C., Gong P. Synthesis and in vitro anti-hepatitis B virus activity of 1H-benzimidazol-5-ol derivatives[J] Chinese Chemical Letters. 2010, 21(11): 1326-1329.
[56] Shaw A. Y., Chang, C. Y., Hsu M. Y., Lu P. J., Yang C. N., Chen H. L., Lo C.W., Shiau C. W., Chern M. K. Synthesis and structure-activity relationship study of 8-hydroxyquinoline-derived Mannich bases as anticancer agents[J]. European Journal of Medicinal Chemistry, 2010, 45(7):2860-2867.
[57] Chantarasiri N, Ruangpornvisuti V, Muangsin N, Structure and physico-chemical properties of hexadentate Schiff base zinc complexes derived from salicylaldehydes and triethylenetetramine[J] Journal of Molecular Structure, 2004, 701 (1): 93-103.
[58]张英菊,吕小兵.环己二胺手性席夫碱配体的合成与表征[J]合成化学, 2005, 13(1): 64-66.
[59] SUN Y, TANG N. Enantioselective epoxidation of olefins catalyzed by chiral dimeric and partially water-soluble monomeric Salen-Mn(III) complexes in the presence of novel co-catalysts[J].J. Mol. Catal. A: Chem., 2006, 255 (1): 171-179.
[60] MOBIAN P., KERN J. M., SAUVAGE J. P. Catenane Constructed around a Ru(Diimine)32+ complex used as a template[J] J. Am. Chem. Sol., 2003, 125 (2): 2016-2017.
[61] Ma H., Chen S. H., Studies on Electrochemical Behavior of Copper in Aerated NaBr Solutions with Schiff Base[J]. J. Electrochem. Soc., 2001, 148 (5): 208-216.
[62] Mizuno T., Yamamoto M., Takeuchi M., Sugar chirality sensing using a prochiral Salen-Co(II) complex[J]. Tetrahedron, 2000, 56 (34): 6193-6198.
[63]李连生,吴琉林.手性(Salen)Co在不对称催化反应和天然产物合成中的应用[J].有机化学, 2000, 20(5): 689-700.
[64] Shldon R. A., Koehi J. K., Metal catalysed oxidations of organic compounds [M]. New York: Academic Press. 1981, 97: 102-105.
[65] Ding L. Q., Chu Z., Chen L. L., Lue X. Q., Yan B., Song J. R., Fan D. D., Bao F. Pd- Salen and Pd-Salan complexes: Characterization and application in styrene polymerization[J]. Inorganic Chemistry Communications, 2011, 14(4), 573-577.
[66] Kemper S., Hrobarik P., Kaupp M., Schloerer N. E. Jacobsen's Catalyst for Hydrolytic Kinetic Resolution: Structure Elucidation of Paramagnetic Co(III) Salen Complexes in Solution via Combined NMR and Quantum Chemical Studies. Journal of the American Chemical Society, 2009, 131(12), 4172-4173.
[67] Huhta, T. A., Farrell J. R., Multidentate aminophenol ligands synthesized using Mannich condensations. Abstracts of Papers, 241st ACS National Meeting United States, March, 2011, 27-31.
[68] Abdul-Ghani, A. J., Al-Jeboori, M, J., Al-Karawi A. J. M. Synthesis and spectral studies of new N2S2 and N2O2 Mannich base ligands and their metal complexes. Journal of Coordination Chemistry, 2009, 62(16): 2736-2744.
[69] Maurya M. R., Khurana S. R. D. Six-coordinated oxovanadium(V) complexes of reduced Schiff bases derived from amino acids: synthesis, reactivity and redox studies[J]. Transition Metal Chemistry, 2003, 28(5):511-517.
[70] Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution, University of G?ttingen, Germany 1990.
[71] Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement, University of G?ttingen, Germany 1997.
[72] Dai H. F., Chen C. H., Chen C. S., Yeh W. Y. Synthesis and Characterization of the Triple Cluster (Cp3Fe4(CO)4(C5H4CH=NCH2CH2))3N and Its Function as a Tripodal Tetradentate[J] Ligand Organometallics[J] 2011, 30(10): 2889-2892.
[73] Musa M. A. Khan M. O., Aspedon A., Cooperwood J. S. Synthesis and antimicrobial activity of N, N'– Bis (2-hydroxylbenzyl) - 1, 2 - ethanediamine derivatives[J]. Letters in Drug Design & Discovery 2010, 7(3): 165-170.
[74] Luo H. T., Kang Y., Li Q., Yang L. M. Sulfamic acid as efficient and reusable catalytic system for the synthesis of pyrrole, furan, and thiophene derivatives[J]. Heteroatom Chemistry, 2008, 19(2): 144-148.
[75] Previtera T., Vigorita M. G., Basile M., Fenech, G., Trovato A., Occhiuto F., Monforte M. T., Barbera R., 3,3'-Di(1,3-thiazolidin-4-one) system. V. Synthesisand pharmacological properties of 3,3'(1,2-ethanediyl)bis(2-heteroaryl-1, 3-thiazolidin-4- one) derivatives[J]. European Journal of Medicinal Chemistry 1990, 25(7): 569-579.
[76]张雄,蔡丽华,黄丽芬,朱静静.糠醛双Schiff碱及其铜配合物的合成与抗菌活性研究[J]化学与生物工程, 2010, 27(4): 152-155.
[77] Lanznaster M.; Neves A., Bortoluzzi, A. J., Assumpcao A. M. C., Vencato I., Machado, S. P., Drechsel S. M. Electronic Effects of Electron-Donating and -Withdrawing Groups in Model Complexes for Iron-Tyrosine-Containing Metalloenzymes[J]. Inorganic Chemistry, 2006, 45(3): 1005-1011.
[78] Rajasekar M., Sreedaran S., Prabu R., Narayanan V., Jegadeesh R., Raaman N., Rahiman A. K. Synthesis, characterization, and antimicrobial activities of nickel(II) and copper(II) Schiff-base complexes[J]. Journal of Coordination Chemistry, 2010, 63(1): 136-146.
[79] Wang W., Zhang F. X., Li J., Zhang R. L. New complex of manganese(II) with Schiff base derived from furaldehyde and diethylenetriamine[J]. Russian Journal of Coordination Chemistry, 2010, 36(5): 378-380.
[80] Ali M. A., Bose R. N. Transition metal complexes of furfural and benzil Schiff bases derived from S-benzyldithiocarbazate[J]. Polyhedron, 1984, 3(5): 517-522.
[81] Tudisco C., Sfrazzetto G. T., Pappalardo A., Motta A., Tomaselli G. A., Fragala I. L., Ballistreri F. P., Condorelli G. G. Covalent Functionalization of Silicon Surfaces with a Cavitand- Modified Salen[J]. European Journal of Inorganic Chemistry, 2011, (13): 2124-2131.
[82] Yun X., Hu X. B, Jin Z., Hu J., Yan C.; Yao J., Li H. Copper- Salen catalysts modified by ionic compounds for the oxidation of cyclohexene by oxygen[J]. Journal of Molecular Catalysis A: Chemical, 2010, 327(1-2): 25-31.
[83]王英,徐小平,姚英明,纪顺俊. 1,2二[3-(6-甲基-8-叔丁基-3,4-二氢-1,3苯并噁嗪)基]乙烷与新型双氮桥联四酚化合物的合成[J].合成化学,2010, 18(6): 715-717.
[84] Diego S. A., Hugo K., Rodrigo R., Ramiro A., Fernando G., Maria T. G. Fuentealba Heterobimetallic RePd complexes bridged byη~1:η~5-Ph_2PC_5_H_4 ligand. Synthesis, electronic and crystal structure of (CO)2(PR_3)(η_5-C_5H_4PPh_2)Re–PdCl_2, R = Me and Ome[J] Dalton Trans., 2010,39: 6295-6301.
[85] Al-Gharabli S. I., Ebraheem K. A. K., Mubarak M. S. Synthesis and chelation properties of a new copper selective Mannich polymer containing a 2,4-dihydroxybenzaldoxime group[J]. Journal of Saudi Chemical Society, 2001, 5(3): 399-406.
[86] Park S.; Piyachaturawat P., Taylor A. E., Huang C. Potential N-nitrosodimethy -lamine (NDMA) formation from amine-based water treatment polymers in the reactions with chlorine-based oxidants and nitrosifying agents[J]. Water Science & Technology: Water Supply, 2009, 9(3), 279-288.
[87] Stark J. L., Johnson K. B. Additive useful for stabilizing fuel oils.[P] WO 2009046192
[88]徐秀娟,陈光旭.用酮作为酸组分的Mannich碱的合成[J].有机化学,1985, 4, 284-296.
[89]黎刚,祁健,杨芳,刘荣,张松梅.以哌嗪做连接的壬基酚聚氧乙烯醚三聚表面活性剂[P]. 200910069618.2
[90]徐晶.高分子席夫碱的合成与应用[D].大连轻工业学院,大连:2006
[91] Kais A. K. E., Mohammad S. M., Samer I. A. Synthesis And Chelation Properties Of Some New Mannich Condensation Polymers Containing A Salicylaldoxime Group[J]. Journal of Macromolecular Science: Pure and Applied Chemistry, 2002, 39: 217-229.
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