Studies on the intramolecular cycloaddition reaction of mesoionics derived from the rhodium (II)-catalyzed cyclization of diazoimides

…, DL Hertzog, WR Nadler, MH Osterhout…

Index: Padwa, Albert; Hertzog, Donald L.; Nadler, William R.; Osterhout, Martin H.; Price, Alan T. Journal of Organic Chemistry, 1994 , vol. 59, # 6 p. 1418 - 1427

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Citation Number: 75

Abstract

A series of alkenyl-substituted imides were prepared by treating the appropriate amide with 2, 2, 6-trimethyl-4H-1, 3-dioxen-4-one in xylene at 140 OC to give the N-acetoacylated imides. Exposure of these imides to standard diazo transfer conditions gave the desired diazoimides. The carbenoid intermediate derived by treatment of the diazoimide with rhodium (I1) acetate undergoes ready cyclization onto the neighboring amide carbonyl ...