The Journal of Organic Chemistry

Reactions of vinyl chloroformate and oxime chloroformates with silver salts

P Beak, JA Barron

Index: Beak,P.; Barron,J.A. Journal of Organic Chemistry, 1973 , vol. 38, # 16 p. 2771 - 2775

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Citation Number: 7

Abstract

Vinyl chloroformate (1) reacts with silver acetate in chlorobenzene at 60'to give 17% vinyl acetate (2) and 65% divinyl carbonate (3). Under the same conditions 1 reacts with silver trifluoroacetate to give 77% vinyl trifluoroacetate (4). The latter reaction is shown on the basis of 1* 0 labeling to proceed with retention of the carbon-oxygen bond and is considered to involve a carbonate intermediate. In the presence of tetramethylurea, vinyl ...