Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic. pi.-Systems

A Padwa, DL Hertzog, WR Nadler

Index: Padwa, Albert; Hertzog, Donald L.; Nadler, William R. Journal of Organic Chemistry, 1994 , vol. 59, # 23 p. 7072 - 7084

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Citation Number: 77

Abstract

A series of furanyl-, thienyl-, and indolo-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium (I1) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the ...

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