Nitrene Insertion into a CH Bond at an Asymmetric Carbon Atom with Retention of Optical Activity. Thermally Generated Nitrenes

G Smolinsky, BI Feuer

Index: Smolinsky,G.; Feuer,B.I. Journal of the American Chemical Society, 1964 , vol. 86, p. 3085 - 3088

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Citation Number: 54

Abstract

This work is concerned with the nature of the electronic state of the reacting nitrene Three different types of optically active azides were prepared, an o-azidoalkylbenzene, an alkyl azidocarbonate, and an alkanesulfonyl azide. Pyrolysis of the azides led in each case to cyclization at the asymmetric carbon atom to give an indoline, an oxazolone, and a sultam, respectively. The indoline and ovazolone were shown still to be optically active, and thus it ...