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Synlett 2000; 2000(8): 1187-1189
DOI: 10.1055/s-2000-6766
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Stereochemistry in the Bromination Reaction of 2,7-Dialkyl-3-hydroxyoxepane System Induced by R3P-Br2 Complex

Kenshu Fujiwara* , Masanori Kobayashi, Daisuke Awakura, Akio Murai
  • *Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan; Fax + 81-11-706-27 14; E-mail: amurai@sci.hokudai.ac.jp
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Publication Date:
31 December 2000 (online)

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The bromination reactions of r-2,t-3,c-7-2,7-dialkyl-3-hydroxyoxepane induced by several R3P-Br2 complexes gave the 3-bromooxepane with retention of C3-configuration and a ring-contracted 2-(1-bromoalkyl)oxane. The production of both bromides could be explained by the presence of a hypothetical bicyclic oxonium ion intermediate having two reactive sites. Stereochemical requirement of the substrate for this oxygen-assisted reaction was also clarified.

bromination - neighboring-group effect - phosphorous reagent - ring contraction - stereoselective reaction