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Synlett 1997; 1997(7): 793-794
DOI: 10.1055/s-1997-5782
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Equilibrium in Ring Expansion Reactions of the Bromo Epoxides

Nobuyuki Hayashi, Kenshu Fujiwara, Akio Murai*
  • *Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060, Japan
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Publication History

Publication Date:
31 December 2000 (online)

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AgOTf-promoted ring expansion reaction of 1-bromo-4,5-epoxide effected preferential formation of the oxane derivative both kinetically and thermodynamically. In the reaction with 1-bromo-5,6-epoxide, on the other hand, the oxepane derivative was kinetically favored, and the oxane derivative was thermodynamically preferable.

ring expansion - bromo epoxide - equilibrium - skeletal rearrangement

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