The Journal of Organic Chemistry

Halogenated ketenes. 35. Cycloadditions of halogenated ketenes and tetramethoxyethylene. Semisquaric acid derivatives

WT Brady, RD Watts

文献索引：Brady, William T.; Watts, Ronald D. Journal of Organic Chemistry, 1980 , vol. 45, # 17 p. 3525 - 3527

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被引用次数: 12

摘要

A mechanism is proposed for this acid-catalyzed ringopening reaction as illustrated in Scheme 111. This mechanism involves the protonation of the cyclobutanone at the carbonyl oxygen and ring opening to form the enol carbonium ion, followed by nucleophilic attack of water with the subsequent loss of a proton and methanol to yield the enol ester. Tautomerization of the enol ester results in the formation of the keto ester. The presence of ...