Ozonolysis of vinyl ethers. Evidence for intramolecular oxygen transfer from a carbonyl oxide moiety to a methoxyvinyl group

…, M Nojima, S Kusabayashi

Index: Nakamura, Norinaga; Nojima, Masatomo; Kusabayashi, Shigekazu Journal of the American Chemical Society, 1987 ,  vol. 109,  # 16  p. 4969 - 4973

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Citation Number: 23

Abstract

Abstract: Ozonolysis of diene 1 in carbon tetrachloride gave exclusively the keto ester 2, while in methanol the keto olefin 17 was the major product. The behavior of model vinyl ethers 3a, b has revealed that a mechanism involving intramolecular oxygen atom transfer from the carbonyl oxide moiety to a methoxyvinyl group is the most probable for the keto ester formation from diene 1.