On The Reactivity Of α-(triphenylphosphoranylidene)-benzylphenylketene With Nitrogen Compounds. Synthetic And Mechanistic Implications

The reactivity of α-(triphenylphosphoranylidene)-benzylphenylketene, a stabilized phosphorus ylide derived from diphenylcyclopropenone, toward nitrogen compounds was investigated. Particularly, the reaction of diethyl azodicarboxylate with α-(triphenylphosphoranylidene)-benzylphenylketene provides a new route to polysubstituted N-acyl carbamates.135687691Cunha, S., Kascheres, A., (2001) J. Braz. Chem. Soc., 12, p. 481. , and references thereinKascheres, A., Joussef, A.C., Duarte, H.C., (1983) Tetrahedron Lett., 24, p. 1837Hamada, A., Takizawa, T., (1975) Chem. Pharm. Bull., 23, p. 2938Hamada, A., Takizawa, T., (1972) Tetrahedron Lett., 13, p. 1849Obata, N., Takizawa, T., (1970) Tetrahedron Lett., 11, p. 2231Kelly, S.E., (1991) Comprehensive Organic Synthesis, 1. , Trost, B. M.Fleming, I., eds.Pergamon Press: OxfordMeshram, H.M., Reddy, G.S., Reddy, M.M., Yadav, J.S., (1998) Tetrahedron Lett., 39, p. 4107Aitken, R.A., Karodia, N., (1997) Liebigs Ann. Recl., p. 779Aitken, R.A., Karodia, N., (1998) Tetrahedron, 54, p. 9223Smith, M.B., (1994) Organic Synthesis, p. 782. , McGraw-Hill, Inc.: SingaporeCunha, S., Kascheres, A., (2000) J. Braz. Chem. Soc., 11, p. 525Kascheres, A., Rodrigues, J.A.R., (1975) J. Org. Chem., 40, p. 1440Kascheres, A., Marchi D., Jr., (1975) J. Org. Chem., 40, p. 2985Kascheres, A., Correa Filho, J., Cunha, S., (1993) Tetrahedron, 49, p. 381Gösl, R., Neuwsen, A., (1963) Org. Synth., 43, p. 1Balasubramanian, A., McIntosh, J.M., Snieckus, V., (1970) J. Org. Chem., 35, p. 433Westwood, N.B., Walker, R.T., (1998) Tetrahedron, 54, p. 13391Wyatt, P.G., Anslow, A.S., Coomber, B.A., Cousins, R.P.C., Evans, D.N., Gilbert, V.S., Humber, D.C., Weingarten, G.G., (1995) Nucleosides Nucleotides, 14, p. 2039Chua, S.-G., Cook, M.J., Katritzky, A., (1974) J. Chem. Soc., Perkin Trans. 2, p. 546Breslow, R., Eicher, T., Peterson, R.A., Krebs, A., Posner, J., (1965) J. Am. Chem. Soc., 87, p. 1320Poyla, J.B., Spotswood, T.M., (1948) Rec. Trav. Chim., 67, p. 927Toda, F., Mitote, T., Akagi, K., (1969) Bull. Chem. Soc. Jpn., 31, p. 177