The Chemistry of N-CO2 Bonds: Synthesis of Carbamic Acids and Their Derivatives, Isocyanates, and Ureas

Carbon Dioxide as Chemical Feedstock

Volumn , Issue , 2010, Pages 121-167

  Quaranta, Eugenio ^a   Aresta, Michele ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Alkylammonium carbamates; Carbamate esters; Carbamation reactions; Carbamic acids; Carbon dioxide; Isocyanates; Ureas

Indexed keywords

EID: 84857164428     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527629916.ch6     Document Type: Chapter

References (305)

1. Aresta, M. and Quaranta, E. (1993) Proceedings of International Conference on Carbon Dioxide Utilization, Bari, Italy, pp. 63-77.
2. Belli Dell 'Amico, D., Calderazzo, F., Labella, F., Marchetti, F., and Pampaloni, G. (2003) Chem. Rev., 103, 3857.
3. Hill, M.R., Jensen, P., Russell, J.J., and Lamb, R.N. (2008) Dalton Trans., 2751
4. Notni, J., Schenck, S., Goerls, H., Breitzke, H., and Anders, E. (2008) Inorg. Chem., 47, 1382.
5. Baisch, U., Pagano, S., Zeuner, M., and Schnick, W. (2006) Eur. J. Inorg. Chem., 3517.
6. Verdejo, B., Aguilar, J., Garcia-Espana, E., Gavina, P., Latorre, J., Soriano, C., Linares, J.M., and Domenech, A. (2006) Inorg. Chem., 45, 3803.
7. Malik, M.A., O'Brien, P., Motevalli, M., and Abrahams, I. (2006) Polyhedron, 25, 241.
8. McCowan Shawn, C. and Caudle, M.T. (2005) Dalton Trans., 238.
9. Caudle, M.T., Brennessel, W.W., and Young, V.J. (2005) Inorg. Chem., 44, 3233.
10. Bramsen, F., Bond, A.D., McKenzie, C.J., Hazell, R.G., Moubaraki, B., and Murray, K.S. (2005) Chem. Eur. J., 11, 825.
11. Dell 'Amico Belli, D., Calderazzo, F., Englert, U., Labella, L., Marchetti, F., and Specos, M. (2004) Eur. J. Inorg. Chem., 3938.
12. Aresta, M., Dibenedetto, A., and Quaranta, E. (1995) J. Chem. Soc. Dalton Trans., 3359.
13. Aresta, M. and Quaranta, E. (1995) J. Organomet. Chem., 488, 211.
14. Tang, Y., Zackarov, L.N., Rheingold, A.L., and Kemp, R.A. (2004) Organometallics, 23, 4788.
15. Lill Nilsson, S.O., Kohn, U., and Anders, E. (2004) Eur. J. Org. Chem., 2868.
16. Tang, Y., Kassel, W.S., Zakharov, L.N., Rheingold, A.L., and Kemp, R.A. (2005) Inorg. Chem., 44, 359.
17. Mendiratta, A., Cummins, C.C., Cotton, F.A., Ibragimov, S.A., Murillo, C.A., and Villagran, D. (2006) Inorg. Chem., 45, 4328.
18. Himmel, H.J. (2007) Z. Anorg. Allg. Chem., 633, 2191.
19. Zeuner, M., Pagano, S., and Schnick, W. (2008) Chem. Eur. J., 14, 1524.
20. Bart, S.C., Anthon, C., Heinemann, F.W., Bill, E., Edelstein, N.M., and Meyer, K. (2008) J. Am. Chem. Soc., 130, 12536.
21. Aresta, M. and Quaranta, E. (1988) J. Org. Chem., 53, 4153.
22. Aresta, M. and Quaranta, E. (1988) Italian Patent 1198206.
23. Aresta, M. and Quaranta, E. (1992) J. Chem. Soc. Dalton Trans., 1893.
24. Shi, M., Jiang, J.K., Shen, Y.M., Feng, Y.S., and Lei, G.X. (2000) J. Org. Chem., 65, 3443.
25. Shi, M., Shen, Y.M., and Jiang, J.K. (2001) Chin. J. Chem., 19, 405.
26. Adams, P. and Baron, F.A. (1965) Chem. Rev., 65, 567.
27. Hagemann, C. (1983) Methoden der Organischen Chemie, 4th edn (ed. Houben-Weil), Georg Thieme Verlag, Stuttgart, vol. E 4, p. 64.
28. Rossi, L. (2005) Sci. Synth., 18, 461.
29. Gallou, I. (2007) Org. Prep. Proced. Intern., 39, 355.
30. Sartori, G. and Maggi, R. (2005) Sci. Synth., 18, 665.
31. Braunstein, P. (1989) Chem. Rev., 89, 1927.
32. Twichett, H. (1974) Chem. Soc. Rev., 3, 209.
33. Cotarca, L. and Eckert, H. (2004) Phosgenations-A Handbook, Wiley-VCH Verlag GmbH, Weinheim.
34. Aresta, M. and Quaranta, E. (1997) Chem. Tech., 27 (3), 32.
35. Carafa, M. and Quaranta, E. (2009) Mini-Rev. Org. Chem., 6, 168.
36. Midvan, A.S., Fry, D.C., and Serpesu, E.H. (1990) Enzymatic and Model Carboxylations and Reactions for Carbon Dioxide Utilization (eds M. Aresta and J.V. Schloss), Kluwer, Dordrecht, p. 211.
37. Cleland, W.W., Andrews, T.J., Gutteridge, S., Hartmann, F.C., and Lorimer, G.H. (1998) Chem. Rev., 98, 549.
38. Schimming, V., Hoelger, C.G., Buntkowsky, G., Sack, I., Fuhrhop, J.H., Rocchetti, S., and Limbach, H.H. (1999) J. Am. Chem. Soc., 121, 4892.
39. Goettmann, F., Thomas, A., and Antonietti, M. (2007) Angew. Chem., Int. Ed., 46, 2717.
40. Terlouw, J.K. and Schwarz, H. (1987) Angew. Chem., Int. Ed. Engl., 26, 805.
41. Khanna, R.K. and Moore, M.H. (1999) Spectrochim. Acta Part A, 55, 961.
42. Kaminskaia, N.V. and Kostic, N.M. (1997) Inorg. Chem., 36, 5917.
43. Remko, M., Liedl, K.R., and Rode, B.M. (1993) J. Chem. Soc. Faraday Trans., 89, 2375.
44. Remko, M. and Rode, B.M. (1995) J. Mol. Struct. (THEOCHEM), 339, 125.
45. Wen, N. and Brooker, M.H. (1995) J. Phys. Chem., 99, 359.
46. Jamroz, M.H., Dobrowolski, J.Cz., and Borowiak, M. (2000) Vib. Spectrosc., 22, 157.
47. Jamroz, M.H. and Dobrowolski, J. Cz. (2002) Vib. Spectrosc., 29, 217.
48. Aresta, M., Ballivet Tkatchenko, D., Belli Dell 'Amico, D., Bonnet, M.C., Boschi, D., Calderazzo, F., Faure, R., Labella, L., and Marchetti, F. (2000) Chem. Commun., 1099.
49. Jamroz, M.H., Dobrowolski, J.Cz., Rode, J.E., and Borowiak, M. (2002) J. Mol. Struct. (THEOCHEM), 618, 101.
50. Radeglia, R., Andersch, J., and Schroth, W. (1989) Z. Naturforsch., 44b, 181.
51. Masuda, K., Ito, Y., Horiguchi, M., and Fujita, H. (2005) Tetrahedron, 61, 213.
52. Hampe, E.M. and Rudkevich, D.M. (2003) Tetrahedron, 59, 9619.
53. Wittmann, K., Wisniewski, W., Mynott, R., Leitner, W., Kranermann, C.L., Rische, T., Eilbracht, P., Kluwer, S., Ernsting, J.M., and Elsevier, C.J. (2001) Chem. Eur. J., 7, 4584.
54. Furstner, A., Ackermann, L., Beck, K., Hori, H., Koch, D., Langemann, K., Liebl, M., Six, C., and Leitner, W. (2001) J. Am Chem. Soc., 123, 9000.
55. Xie, X., Liotta, C.L., and Eckert, C.A. (2004) Ind. Eng. Chem. Res., 43, 7907.
56. Fischer, H., Gyllenhaal, O., Vessmann, J., and Albert, K. (2003) Anal. Chem., 75, 622.
57. Dijkstra, Z.J., Doornbos, A.R., Weyten, H., Ernsting, J.M., Elsevier, C.J., and Keurentjes, J.T.F. (2007) J. Supercrit. Fluids, 41, 109.
58. Kayaki, Y., Suzuki, T., and Ikariya, T. (2008) Chem. Asian J., 3, 1865.
59. Aresta, M., Dibenedetto, A., Quaranta, E., Dibenedetto, A., Tommasi, I., and Marciniec, B. (2000) Appl. Organometal. Chem., 14, 871.
60. Dibenedetto, A., Aresta, M., Fragale, C., and Narracci, M. (2002) Green Chem., 4, 439.
61. Alauzun, J., Besson, E., Mehdi, A., Reye, C., and Corriu, R.J.P. (2008) Chem. Mater., 20, 503.
62. Smola, A. (1948) Mitt. Chem. Forsch. Inst. Ind. Oesterr., 2, 38.
63. Neda, I., Kaukorat, T., and Fischer, A.K. (2003) Eur. J. Org. Chem., 3784.
64. Aresta, M. and Quaranta, E. (1993) Italian Patent 1237208.
65. Aresta, M. and Quaranta, E. (1992) Tetrahedron, 48, 1515.
66. Danckwerts, P.V. (1979) Chem. Eng. Sci., 34, 443.
67. Crooks, J.E. and Donnellan, J.P. (1989) J. Chem. Soc., Perkin Trans. II, 331.
68. Jamroz, M.H., Dobrowolski, J.Cz., and Borowiak, M. (1997) J. Mol. Struct., 404, 105.
69. Hori, Y., Nagano, Y., Nakao, J., Fukuoka, T., and Taniguchi, H. (1986) Chem. Express, 1, 224.
70. McGhee, W.D., Riley, D., Kevin, C., Pan, Y., and Parnas, B. (1995) J. Org. Chem., 60, 2820.
71. McGhee, W.D., Pan, Y., and Riley, D.P. (1994) J. Chem. Soc. Chem. Commun., 699.
72. McGhee, W.D., Barry, L., Riley, D.P., and Talley, J.J. (1992) European Patent 511948.
73. Kurz, F., Rumpf, B., Sing, R., and Maurer, G. (1996) Ind. Eng. Chem. Res., 35, 3795.
74. Buckingham, A.D., Handy, N.C., Rice, J.E., Somasundram, K., and Dijkgraaf, C. (1986) J. Comput. Chem., 7, 283.
75. Mani, F., Peruzzini, M., and Stoppioni, P. (2006) Green Chem., 8, 995.
76. Filburn, T., Helble, J.J., and Weiss, R.A. (2005) Ind. Eng. Chem. Res., 44, 1542.
77. Bottinger, W., Maiwald, M., and Hasse, H. (2008) Fluid Phase Equilibria, 263, 131.
78. Bates, E.D., Mayton, R.D., Ntai, I., and Davis, J.H., Jr (2002) J. Am. Chem. Soc., 124, 926.
79. Blanchard, L.A., Gu, Z., and Brennecke, J.F. (2001) J. Phys. Chem. B, 105, 2437.
80. Kovvali, A.S. and Sirkar, K.K. (2001) Ind. Eng. Chem. Res., 40, 2502.
81. George, M. and Weiss, R.J. (2001) J. Am. Chem. Soc., 123, 10393.
82. Carretti, E., Dei, L., Baglioni, P., and Weiss, R.G. (2003) J. Am. Chem. Soc., 125, 5121.
83. Stastny, V., Anderson, A., and Rudkevivh, D.M. (2006) J. Org. Chem., 71, 8696.
84. Ki, C.D., Oh, C., Oh, S.G., and Chang, J.Y. (2002) J. Am. Chem. Soc., 124, 14838.
85. Yamada, T., Lukac, P.J., George, M., and Weiss, R.G. (2007) Chem. Mater., 19, 967.
86. Phan, L., Andreatta, J.R., Horvey, L.K., Edie, C.F., Luco, A.L., Mirchandani, A., Darensbourg, D.J., and Jessop, P.J. (2008) J. Org. Chem., 73, 127.
87. Ray, S., Pathak, S.R., and Chaturvedi, D. (2005) Drugs Fut., 30, 161.
88. Gupta, R.C. (2006) Toxicology of Organophosphate and Carbamate Compounds (ed. R.C. Gupta), Elsevier Inc., Burlington, p. 5.
89. Green, T.W. and Wuts, P.G.M. (2007) Protective Groups in Organic Synthesis, John Wiley & Sons, Inc., New York.
90. Buchstaller, H.P. (1998) Tetrahedron, 54, 3465.
91. Ullrich, H. (1983) in Kirk-Othmer, Encyclopedia of Chemical Technology, vol. 23, 3rd edn, John Wiley & Sons Inc., New York, p. 576.
92. Paul, F. (2000) Coord. Chem. Rev., 203, 269.
93. Giannoccaro, P., Dibenedetto, A., Gargano, M., Quaranta, E., and Aresta, M. (2008) Organometallics, 27, 967.
94. Giannoccaro, P., Cornacchia, D., Doronzo, S., Mesto, E., Quaranta, E., and Aresta, M. (2006) Organometallics, 25, 2872.
95. Delledonne, F., Rivetti, F., and Romano, U. (2001) Appl. Cat. A: Gen., 221, 241.
96. Chaturvedi, D. and Ray, S. (2007) Curr. Org. Chem., 11, 987.
97. Tsuda, T., Washita, H., Watanabe, K., Miwa, M., and Saegusa, T. (1978) J. Chem. Soc. Chem. Commun., 815.
98. Belforte, A. and Calderazzo, F. (1989) J. Chem. Soc., Dalton Trans., 1007.
99. Yoshida, Y., Ishii, S., Watanabe, M., and Yamashita, T. (1989) Bull. Chem. Soc. Jpn, 62, 1534.
100. Shi, M. and Shen, Y.M. (2001) Helv. Chim. Acta, 84, 3357.
101. Perez, E.R., Odnicki Da Silva, M., Costa, V.C., Rodriguez-Filho, U.P., and Franco, D.W. (2002) Tetrahedron Lett., 43, 4091.
102. McGhee, W.D. and Talley, J.J. (1994) US Patent 5302717.
103. Butcher, K.J. (1994) Synlett, 825.
104. Salvatore, R.N., Flanders, V.L., Ha, D., and Jung, K.W. (2000) Org. Lett., 2, 2797.
105. Jung, K.W. (2000) WO 0050389.
106. Salvatore, R.N., Shin, S.I., Nagle, A.S., and Jung, K.W. (2001) J. Org. Chem., 66, 1035.
107. Salvatore, R.N., Ledger, J.A., and Jung, K.W. (2001) Tetrahedron Lett., 42, 6023.
108. Salvatore, R.N., Chu, F., Nagle, A.S., Kapxhiu, E.A., Cross, R.M., and Jung, K.W. (2002) Tetrahedron, 58, 3329.
109. Yoshida, M., Hara, N., and Okuyama, S. (2000) Chem. Commun., 151.
110. Singh, K.N. (2007) Synth. Commun., 37, 2651.
111. Chaturvedi, D., Mishra, N., and Mishra, V. (2006) Chinese Chem. Lett., 17, 1309.
112. Chaturvedi, D. and Ray, S. (2005) Lett. Org. Chem., 2, 742.
113. Chaturvedi, D. and Ray, S. (2006) Monatsh. Chem., 137, 201.
114. Chaturvedi, D. and Ray, S. (2006) Monatsh. Chem., 137, 459.
115. Chaturvedi, D., Kumar, A., and Ray, S. (2002) Synth. Commun., 32, 2651.
116. Casadei, M.A., Micheletti Moracci, F., Zappia, G., Inesi, A., and Rossi, L. (1997) J. Org. Chem., 62, 6754.
117. Feroci, M., Inesi, A., and Rossi, L. (2000) Tetrahedron Lett., 41, 963.
118. Feroci, M., Casadei, M.A., Orsini, M., Palombi, L., and Inesi, A. (2003) J. Org. Chem., 68, 1548.
119. Hess, U., Komenda, J., Hollwarth, A., and Dunkel, S. (1992) Pharmazie, 47, 848.
120. Casadei, M.A., Inesi, A., Micheletti Moracci, F., and Rossi, L. (1996) Chem. Commun., 2575.
121. Feroci, M., Orsini, M., Rossi, L., Sotgiu, G., and Inesi, A. (2007) J. Org. Chem., 72, 200.
122. Niu, D.F., Zhang, L., Xiao, L.P., Luo, Y.W., and Lu, J.X. (2007) Appl. Organomet. Chem., 21, 941.
123. Ikeda, S., Takagi, T., and Ito, K. (1987) Bull. Chem. Soc. Jpn, 60, 2517.
124. Calderwood, J.L., Jr, Roberts, T.S., and Sawyer, D.T. (1984) J. Am. Chem. Soc., 106, 4667.
125. Srivastava, R., Manju, M.D., Srinivas, D., and Ratnasamy, P. (2004) Catal. Lett., 97, 41.
126. Srivastava, R., Srinivas, D., and Ratnasamy, P. (2005) Appl. Catal. A: General, 289, 128.
127. Srivastava, R., Srinivas, D., and Ratnasamy, P. (2006) Tetrahedron Lett., 47, 4213.
128. Srivastava, R., Srinivas, D., and Ratnasamy, P. (2005) J. Catal., 233, 1.
129. Srivastava, R., Srinivas, D., and Ratnasamy, P. (2006) Micropor. Mesopor. Mater., 90, 314.
130. Belforte, A., Belli Dell 'Amico, D., and Calderazzo, F. (1988) Chem. Ber., 121, 1891.
131. Belforte, A., Belli Dell 'Amico, D., Calderazzo, F., Giurlani, U., and Labella, L. (1993) Gazz. Chim. Ital., 123, 119.
132. Aresta, M. and Quaranta, E. (1993) Italian Patent 1237207.
133. Aresta, M. and Quaranta, E. (1991) Tetrahedron, 47, 9489.
134. Aresta, M., Dibenedetto, A., Quaranta, E., Boscolo, M., and Larsson, R. (2001) J. Mol. Catal., 174, 7.
135. Aresta, M. and Dibenedetto, A. (2002) Chem. Eur. J., 8, 685.
136. Ishii, S., Nakayama, H., Yoshida, Y., and Yamashita, T. (1989) Bull. Soc. Chem. Jpn, 62, 455.
137. Abla, M., Choi, J.C., and Sakakura, T. (2001) Chem. Commun., 2238.
138. Abla, M., Choi, J.C., and Sakakura, T. (2004) Green Chem., 6, 524.
139. Choi, J.C., Mahamdi, A., and Sakakura, T. (2006) Japanese Patent 022043.
140. Ion, A., Van Doorslaer, C., Parvulescu, V., Jacobs, P., and De Vos, D. (2008) Green Chem., 10, 111.
141. Bratt, M.O. and Taylor, P.C. (2003) J. Org. Chem., 68, 5439.
142. Chaturvedi, D., Kumar, A., and Ray, S. (2003) Tetrahedron Lett., 44, 7637.
143. Chaturvedi, D., Mishra, N., and Mishra, V. (2007) Monatsh. Chem., 138, 57.
144. Soga, K., Hosoda, S., Nakamura, H., and Ikeda, S. (1976) J. Chem. Soc. Chem. Commun., 617.
145. Kawanami, H. and Ikushima, Y. (2002) Tetrahedron Lett., 43, 3841.
146. Kawanami, H., Matsumoto, H., and Ikushima, Y. (2005) Chem. Lett., 34, 60.
147. Du, Y., Wu, Y., Liu, A.H., and He, L.N. (2008) J. Org. Chem., 73, 4709.
148. Nomura, R., Nakano, T., Nishio, Y., Ogawa, S., Ninagawa, A., and Matsuda, H. (1989) Chem. Ber., 122, 2407.
149. Shen, Y.M., Duan, W.L., and Shi, M. (2004) Eur. J. Org. Chem., 3080.
150. Hancock, M.T. and Pinhas, A.R. (2003) Tetrahedron Lett., 44, 5457.
151. Hancock, M.T. and Pinhas, A.R. (2004) Synthesis, 14, 2347.
152. Mu, W.H., Chasse, G.A., and Fang, D.C. (2008) J. Phys. Chem. A, 112, 6708.
153. Sudo, A., Morioka, Y., Koizumi, E., Sanda, F., and Endo, T. (2003) Tetrahedron Lett., 44, 7889.
154. Sudo, A., Morioka, Y., Sanda, F., and Endo, T. (2004) Tetrahedron Lett., 45, 1363.
155. Miller, A.W. and Nguyen, S.T. (2004) Org. Lett., 6, 2301.
156. Tascedda, P. and Dunach, E. (2000) Chem. Commun., 449.
157. Steele, A.B. (1959) US Patent 2868801.
158. Lynn, J.W. (1961) US Patent 2975187.
159. Bhanage, B.M., Fujita, S., Ikushima, Y., and Arai, M. (2003) Green Chem., 5, 340.
160. Matsuda, H., Baba, A., Nomura, R., Kori, M., and Ogawa, S. (1985) Ind. Eng. Chem. Prod. Res. Dev., 24, 239.
161. Tominaga, K. and Sasaki, Y. (2002) Synlett, 307.
162. Fujita, S., Kanamaru, H., Senboku, H., and Arai, M. (2006) Int. J. Mol. Sci., 7, 438.
163. Akasaki, Y., Hatano, S., and Fukuyama, M. (1978) Japanese Patent 78111062.
164. Dozen, Y. and Ukita, M. (1982) Japanese Patent 57042678.
165. Kawanami, H. and Ikushima, Y.J. (2002) Jpn. Petrol. Inst., 45, 321.
166. Feroci, M., Inesi, A., Mucciante, V., and Rossi, L. (1999) Tetrahedron Lett., 40, 6059.
167. Casadei, M.A., Feroci, M., Inesi, A., Rossi, L., and Sotgiu, G. (2000) J. Org. Chem., 65, 4759.
168. Feroci, M., Gennaro, A., Inesi, A., Orsini, M., and Palombi, L. (2002) Tetrahedron Lett., 43, 5863.
169. Kodaka, M., Tomohiro, T., Lee, A.L., and Okuno, H. (1989) J. Chem. Soc. Chem. Commun., 1479.
170. Kodaka, M., Lee, A.L., Tomohiro, T., and Okuno, H. (1990) Chem. Express, 5, 233.
171. Kodaka, M., Tomohiro, T., Lee, A.L., and Okuno, H. (1991) Chem. Express, 6, 217.
172. Ariza, X., Pineda, O., Urpì, F., and Villarasa, J. (2001) Tetrahedron Lett., 42, 4995.
173. Kodaka, M., Tomohiro, T., and Oxuno, H.H. (1993) J. Chem. Soc. Chem. Commun., 81.
174. Dinsmore, C.J. and Mercer, S.P. (2004) Org. Lett., 6, 2885.
175. Kubota, Y., Kodaka, M., Tomohiro, T., and Okuno, H. (1993) J. Chem. Soc., Perkin Trans. I, 5.
176. Yoshida, Y., and Inoue, S. (1978) Bull. Chem. Soc. Jpn, 51, 559.
177. Yoshida, Y. and Inoue, S. (1980) Polym. J., 12, 763.
178. Yoshida, Y., Ishii, S., Kawato, A., Yamashita, T., Yano, M., and Inoue, S. (1988) Bull. Chem. Soc. Jpn, 61, 2913.
179. Yoshida, Y. and Inoue, S. (1978) Chem. Lett., 139.
180. Yoshida, Y. and Inoue, S. (1979) J. Chem. Soc., Perkin Trans. I, 3146.
181. Asano, T., Saito, N., Ito, S., Hatakeda, K., and Toda, T. (1978) Chem. Lett., 311.
182. Kojima, F., Aida, T., and Inoue, S. (1986) J. Am. Chem. Soc., 106, 391.
183. Yoshida, M., Ohshima, M., and Toda, T. (1993) Heterocycles, 35, 623.
184. Karikomi, M., Yamazaki, T., and Toda, T. (1993) Chem. Lett., 1965.
185. Toda, T. (1977) Chem. Lett., 957.
186. Saito, N., Hatakeda, K., Ito, S., Asano, T., and Toda, T. (1986) Bull. Chem. Soc. Jpn, 59, 1629.
187. Ishii, S., Zhou, M., Yoshida, Y., and Noguchi, H. (1999) Synth. Commun., 29, 3207.
188. Yoshida, Y. and Inoue, S. (1977) Chem. Lett., 1375.
189. McGhee, W.D. and Riley, D.P. (1992) Orgamometallics, 11, 900.
190. McGhee, W.D., Riley, D.P., Christ, M.E., and Christ, K.M. (1993) Orgamometallics, 12, 1429.
191. Yoshida, M., Ohsawa, Y., Sugimoto, K., Tokuyama, H., and Masataka, I. (2007) Tetrahedron Lett., 48, 8678.
192. Toda, T. and Kitagawa, Y. (1987) Angew. Chem., Int. Ed. Engl., 26, 334.
193. Sasaki, D. and Dixneuf, P.H. (1986) J. Chem. Soc. Chem. Commun., 790.
194. Mahé, R., Dixneuf, P.H., and Lécolier, S. (1986) Tetrahedron Lett., 27, 6333.
195. Mitsudo, T., Hori, Y., Yamakawa, Y., and Watanabe, Y. (1987) Tetrahedron Lett., 28, 4417.
196. Mahé, R., Sasaki, Y., Bruneau, C., and Dixneuf, P.H. (1989) J. Org. Chem., 54, 1518.
197. Bruneau, C. and Dixneuf, P.H. (1992) J. Mol. Catal., 74, 97.
198. Rohr, M., Geyer, C., Wandeler, R., Schneider, M.S., Murphy, E.F., and Baiker, A. (2001) Green Chem., 3, 123.
199. Sasaki, Y. and Dixneuf, P.H. (1987) J. Org. Chem., 52, 314.
200. Hofer, J., Doucet, H., Bruneau, C., and Dixneuf, P.H. (1991) Tetrahedron Lett., 32, 7409.
201. Jiang, J.L. and Hua, R. (2006) Tetrahedron Lett., 47, 953.
202. Bruneau, C. and Dixneuf, P.H. (1987) Tetrahedron Lett., 28, 2005.
203. Sasaki, Y. and Dixneuf, P.H. (1987) J. Org. Chem., 52, 4389.
204. Shim, S.C., Baeg, J.O., Doh, C.H., Youn, Y.Z., and Kim, T.J. (1990) Bull. Korean Chem. Soc., 11, 467.
205. Kim, T.J., Kwon, K.H., Kwon, S.C., Baeg, J.O., and Shim, S.C. (1990) J. Organomet. Chem., 389, 205.
206. Kim, H.S., Kim, J.W., Kwon, S.C., Shim, S.C., and Kim, T.J. (1997) J. Organomet. Chem., 545-546, 337.
207. Qi, C.R. and Jiang, H.F. (2007) Green Chem., 9, 1284.
208. Dimroth, P., Pasedach, H., and Schefczik, E. (1964) German Patent 1151507.
209. Fournier, J., Bruneau, C., and Dixneuf, P.H. (1990) Tetrahedron Lett., 31, 1721.
210. Zhang, Q., Shi, F., Gu, Y., Yang, J., and Deng, Y. (2005) Tetrahedron Lett., 46, 5907.
211. Gu, Y., Zhang, Q., Duan, Z., Zhang, J., Zhang, S., and Deng, Y. (2005) J. Org. Chem., 70, 7376.
212. Jiang, H., Zhao, J., and Wang, A. (2008) Synthesis, 763.
213. Dimroth, P. and Pasedach, H. (1964) German Patent 1164411.
214. Shi, M. and Shen, Y.M. (2002) J. Org. Chem., 67, 16.
215. Costa, M., Chiusoli, G.P., Taffurelli, D., and Dalmonego, G. (1998) J. Chem. Soc., Perkin Trans. I, 1541.
216. Feroci, M., Orsini, M., Sotgiu, G., Rossi, L., and Inesi, A. (2005) J. Org. Chem., 70, 7795.
217. Kayaki, Y., Yamamoto, M., Suzuki, T., and Ikariya, T. (2006) Green Chem., 8, 1019.
218. Maggi, R., Bertolotti, C., Orlandini, E., Oro, C., Sartori, G., and Selva, M. (2007) Tetrahedron Lett., 48, 2131.
219. Oertel, G. (1985) Polyurethane Handbook, Hanser Publishers, Munich.
220. Randall, D. and Lee, S. (2002) The Polyurethane Book, John Wiley & Sons, Inc.
221. Merger, F. and Towae, F. (1987) US Patent 4713476.
222. Sundermann, R., Konig, K., Engbert, T., Becker, G., and Hammen, G. (1983) US Patent 4388246.
223. Rosenthal, R. and Zajacek, J.G. (1976) US Patent 3962302.
224. Bortnick, N., Luskin, L.S., Hurwitz, M.D., and Rytina, A.W. (1956) J. Am. Chem. Soc., 78, 4358.
225. Spohn, R.J. (1983) GB Patent 2113673.
226. Mironov, V.F., Kozyukov, V.P., and Bulatov, V.P. (1973) Zh. Obshch. Khim., 43, 2089.
227. Kozyukov, V.P., Orlov, G.I., and Mironov, V.F. (1979) Zh. Obshch. Khim., 49, 2155.
228. Szalay, R., Bocskei, Z., Knausz, D., Lovasz, C., Ujszaszy, K., Szakacz, I., and Sohar, P. (1996) J. Organomet. Chem., 510, 93.
229. Alper, H. and Butler, D.C.D. (1998) Chem. Commun., 2575.
230. Alper, H. and Valli, V.L.K. (1995) J. Org. Chem., 60, 257.
231. Chong, P.J., Janicki, S.Z., and Petillo, P.A. (1998) J. Org. Chem., 63, 8515.
232. Kricheldorf, H.R. (1970) Synthesis, 649.
233. Pirkle, W.H. and Rinaldi, P.L. (1978) J. Org. Chem., 43, 3803.
234. Tsuda, T., Sanada, S.I., and Saegusa, T. (1976) J. Organomet. Chem., 116, C10.
235. Kim, W.Y., Chang, J.S., Park, S.E., Ferrence, G., and Kubiak, C.P. (1998) Chem. Lett., 1063.
236. Kim, W.Y., Chang, J.S., Park, S.E., and Kubiak, C.P. (1999) Res. Chem. Intermed., 25, 459.
237. DeLaet, D.L., Fanwick, P.E., and Kubiak, P.C. (1987) J. Chem. Soc. Chem. Commun., 1412.
238. DeLaet, D.L., Fanwick, R., Del Rosario, P.E., and Kubiak, P.C. (1987) J. Am. Chem. Soc., 109, 754.
239. Kubiak, P.C., and Ratliff, K.S. (1991) Israel J. Chem., 31, 3.
240. Ghosh, R. and Samuelson, A.G. (2005) Chem. Commun., 2017.
241. William, A. and Ibrahim, I.T. (1981) Chem. Rev., 81, 589.
242. Birdwhistell, K.R., Boucher, T., Ensminger, M., Harris, S., Johnson, M., and Toporek, S. (1993) Organometallics, 12, 1023.
243. Birdwhistell, K.R., Lanza, J., and Pasos, J. (1999) J. Organomet. Chem., 584, 200.
244. Kilgore, U.J., Basuli, F., Huffmann, J.C., and Mindiola, D.J. (2006) Inorg. Chem., 45, 487.
245. Wadsworth, W.S. and Emmons, W.D. (1964) J. Org. Chem., 29, 2816.
246. Molina, P., Alajarin, M., and Arques, A. (1982) Synthesis, 596.
247. Wannagat, U., Kuckertz, H., Kruger, C., and Pump, J. (1964) Z. Anorg. Allg. Chem., 333, 54.
248. Radkov, Y.F., Fedorova, E.A., Khorshev, S.Y., Kalinina, G.S., Bochkarev, M.N., and Razuvaev, G.A. (1986) Zh. Obshch. Khim., 56, 386.
249. Sita, L.R., Babcock, J.R., and Xi, R. (1996) J. Am. Chem. Soc., 118, 10912.
250. Babcock, J.R., Sands, L.L., Rheingold, A.L., and Sita, L.R. (1999) Organometallics, 18, 4437.
251. Babcock, J.R. and Sita, L.R. (1998) J. Am. Chem. Soc., 120, 5585.
252. Ciruelos, S., Cuenca, T., Gomez, R., Gomez-Sal, P., Manzanero, A., and Royo, P. (1996) Organometallics, 15, 5577.
253. Kloppenburg, L. and Petersen, J.L. (1996) Organometallics, 15, 7.
254. Sellmann, D., Geipel, F., and Heinemann, F.W. (2000) Chem. Eur. J., 6, 4279.
255. Fullmer, B.C., Fan, H., Ink, M., and Caulton, K.G. (2008) Inorg. Chem., 47, 1865.
256. Tsipis, C.A. and Karipidis, P.A. (2005) J. Phys. Chem. A, 109, 8560.
257. Horvath, M.J., Saylik, D., Elmes, P.S., Jackson, W.R., Lovel, C.G., and Moody, K. (1999) Tetrahedron Lett., 40, 363.
258. Saylik, D., Horvath, M.J., Elmes, P.S., Jackson, W.R., Lovel, C.G., and Moody, K. (1999) J. Org. Chem., 64, 3940.
259. Riley, D., McGhee, W.D., and Waldmann, T. (1994) ACS Symp. Ser., 577 (Benign by Design), 122.
260. Waldmann, T.E. and McGhee, W.D. (1994) J. Chem. Soc. Chem. Commun., 957.
261. McGhee, W.D., Paster, M., Riley, D., Ruettimann, K., Solodar, J., and Waldmann, T. (1996) ACS Symp. Ser., 626 (Green Chemistry), 49.
262. McGhee, W.D., Pan, Y., and Talley, J.J. (1994) Tetrahedron Lett., 35, 839.
263. Brederweld, H. (1962) Recl. Trav. Chim. Pays-Bas, 81, 276.
264. Birkofer, L. and Krebs, K. (1968) Tetrahedron Lett., 9, 885.
265. Mironov, V.F., Kozyukov, V.P., Kirilin, A.D., Sheludyakov, V.D., Dergunov, J.J., and Vostokov, L.A. (1975) Zh. Obshch. Khim., 45, 2007.
266. Oertel, G., Holtschmidt, H., and Malz, H. (1964) Chem. Ber., 97, 891.
267. Yoder, C.H., Komoriya, A., Kochanowski, J.E., and Suydam, F.H. (1971) J. Am. Chem. Soc., 93, 6515.
268. Cragg, R.H. and Lappert, M.F. (1966) J. Chem. Soc. A, 82.
269. Ebsworth, E.A.V., Rocktaschel, G., and Thompson, J.A. (1967) J. Chem. Soc. A, 32.
270. Skeludyakov, V.D., Kirilin, A.D., and Mironov, V.F. (1975) Zh. Obshch. Khim., 45, 479.
271. Skeludyakov, V.D., Kirilin, A.D., Gusev, V.A., Sharapov, V.A., and Mironov, V.F. (1976) Zh. Obshch. Khim., 46, 2712.
272. Birkofer, L. and Sommer, P. (1972) J. Organomet. Chem., 35, C15.
273. Knausz, D., Meszticcky, L., Szakacs, B., Csakvari, B., and Ujszaszy, K. (1983) J. Organomet. Chem., 256, 11.
274. Zoeckler, M.T. and Laine, M.R. (1983) J. Org. Chem., 43, 2539.
275. Lipshutz, B.H., Papa, P., and Keith, J.M. (1999) J. Org. Chem., 64, 3792.
276. Fuchter, M.J., Smith, C.J., Tsang, M.W.S., Boyer, A., Saubern, S., Ryan, J.H., and Holmes, A.B. (2008) Chem. Commun., 2152.
277. Jimenez, G., Rodriguez, E., Gomez Sal, P., Royo, P., Cuenca, T., and Galakhov, M. (2001) Organometallics, 20, 2459.
278. Yamazaki, N., Tomioka, T., and Higashi, F. (1975) Synthesis, 384.
279. Ion, A., Parvulescu, V., Jacobs, P., and De Vos, D. (2007) Green Chem., 9, 158.
280. Ogura, H., Takeda, K., Tokue, R., and Kobayashi, T. (1978) Synthesis, 394.
281. Aresta, M., Dibenedetto, A., Fracchiolla, E., Giannoccaro, P., Pastore, C., Papai, I., and Schubert, G. (2005) J. Org. Chem., 70, 6177.
282. Cooper, C.F. and Falcone, S.J. (1995) Synth. Commun., 25, 2467.
283. Yamazaki, N., Higashi, F., and Iguchi, T. (1974) Tetrahedron Lett., 15, 1191.
284. Yamazaki, N., Iguchi, T., and Higashi, F. (1975) Tetrahedron, 31, 3031.
285. Yamazaki, N., Tomioka, T., and Higashi, F. (1976) Bull. Chem. Soc. Jpn, 49, 3104.
286. Yamazaki, N., and Yamaguchi, M. (1979) Synthesis, 355.
287. O'Brien, R.A., Worman, J.J., and Olson, E.S. (1992) Synth. Commun., 22, 823.
288. Uhrich, K., Olson, E.S., and Worman, J.J. (1986) Synth. Commun., 16, 1387.
289. Porwanski, S., Menuel, S., Marsura, X., and Marsura, A. (2004) Tetrahedron Lett., 45, 5027.
290. Chaturvedi, D., Mishra, N., and Mishra, V. (2008) Monatsh. Chem., 139, 267.
291. Fichter, F. and Becker, B. (1911) Ber. Dtsch. Chem. Ges., 44, 473.
292. Morino, S., Sakai, M., Kashiki, I., Suzuki, A., and Miki, M. (1978) Hokkaido Daigaku Suisangakubu Kenkyu Iho, 29, 75.
293. Mulvaney, J.F. and Evans, R.L. (1948) J. Ind. Eng. Chem., 40, 393.
294. Shi, F., Deng, Y., SiMa, T., Peng, J., Gu, Y., and Qiao, B. (2003) Angew. Chem., Int. Ed., 42, 3257.
295. Jiang, T., Ma, X., Zhou, Y., Liang, S., Zhang, J., and Han, B. (2008) Green Chem., 10, 465.
296. Morimoto, Y., Fujiwara, Y., Taniguchi, H., Hori, Y., and Nagano, Y. (1986) Tetrahedron Lett., 27, 1809
297. Tai, C.C., Huck, M.J., McKoon, E.P., Woo, T., and Jessop, P.G. (2002) J. Org. Chem., 67, 9070.
298. Nomura, R., Yamamoto, M., and Matsuda, H. (1987) Ind. Eng. Chem. Res., 26, 1056.
299. Nomura, R., Hasegawa, Y., Toyosaki, T., and Matsuda, H. (1992) Chem. Express, 7, 569.
300. Nomura, R., Hasegawa, Y., Ishimoto, M., Toyosaki, T., and Matsuda, H. (1992) J. Org. Chem., 57, 7339.
301. Sasaki, Y. and Kagawa, H. (1989) Kogai Shigen Kenkyusho Iho, 18, 13.
302. Fournier, J., Bruneau, C., Dixneuf, P.H., and Lécolier, S. (1991) J. Org. Chem., 56, 4456.
303. Shi, F., Zhang, Q., Na, Y., He, Y., and Deng, Y. (2005) J. Am. Chem. Soc., 127, 4182.
304. Seki, T., Kokubo, Y., Ichikawa, S., Suzuki, T., Kayaki, Y., and Ikariya, T. (2009) Chem. Commun., 349.
305. Bazarov, A.I. (1870) J. Prakt. Chem., 2, 283.