Formation of unsaturated carbenes by alkaline treatment of N-nitrosooxazolidones

MS Newman, AOM Okorodudu

Index: Newman,M.S.; Okorodudu,A.O.M. Journal of Organic Chemistry, 1969 , vol. 34, # 5 p. 1220 - 1224

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Citation Number: 28

Abstract

Treatment of 5, bdisubstituted N-nitrosooxazolidones with alkoxides initiates a series of reactions which are best explained by postulating the formation of unsaturated carbenes,: C= C&. The latter react with olefins, such as cyclohexene or alkyl vinyl ethers, to yield disubstituted methylenecyclopropanes, and with alcohols, ROH, by insertion into the 0-H bond to yield vinyl ethers, R&= CHOR '(see Table I). Treatment of 3-nitroso-l-oxa-3- ...