The Journal of Organic Chemistry

Mechanism of cycloaddition of nitroso compounds with diphenylketene

RC Kerber, MC Cann

Index: Kerber,R.C.; Cann,M.C. Journal of Organic Chemistry, 1974 , vol. 39, p. 2552 - 2558

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Citation Number: 20

Abstract

The cycloaddition of aromatic nitroso compounds pX-CsH4NO with diphenylketene occurs in all cases rapidly and with relatively low regioselectivity, which is little affected by solvents or substituents. With X= CH30. CH3, H, and CHaOzC, the principal product is the 2-aryl-4, 4- diphenyl-l, Z-oxazetidin-3-one. The isomeric oxazetidin-4-one, the main primary product for X=(CH3) 2S, is unstable in all cases and decomposes to car-bon dioxide and a Schiff ...