Cycloaddition of nitrones with allenes. An example of steric control of regiochemistry

…, M Matzinger, MK Venkatramanan

Index: Padwa, Albert; Kline, Donald N.; Koehler, Konrad F.; Matzinger, Michael; Venkatramanan, M. K. Journal of Organic Chemistry, 1987 ,  vol. 52,  # 17  p. 3909 - 3917

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Citation Number: 72

Abstract

A study of the cycloaddition behavior of a series of electron-deficient allenes with C-phenyl- N-alkylnitrones has been carried out. The 1, 3-dipoh cycloaddition proceeds in high yield with complete regiospecificity to produce 5-methylene substituted isoxazolidines. The reactions follow frontier orbital predictions. The orientation has been explained in terms of maximum orbital overlap of the nitrone HOMO-allene LUMO. In certain cases ...