Reaction of acylisocyanates with unsaturated ethers

Abstract

1. The trifluoroacetyl and trichloroacetyl isocyanates react with allyl vinyl and vinyl phenyl ethers to give linear adducts of general formula R1CONHCOCH=CHOR2. Benzoyl isocyanate reacts in a similar manner with allyl vinyl ether. 2. The trifluoroacetyl and trichloroacetyl isocyanates react with p-tolyl vinyl sulfide and p-bromophenyl vinyl sulfide, while benzoyl isocyanate reacts with phenyl vinyl ether, to give the corresponding substituted dihydro -1,3 -oxazin-4-ones. 3. An NMR study of the reactions of the geometric isomers of butenyl ethyl ether with trichloroacetyl isocyanate confirmed that fact that the formation of the linear isomers proceeds via intermediate 4- and 6-membered cyclic compounds. © 1975 Plenum Publishing Corporation.