Hyperconjugative effects in the stereoselective ring-opening reactions of oxetenoxides

Seiji Mori, Mitsuru Shindo

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)


(Chemical Equation Presented) Unexpectedly, the pattern of the stereoselectivity in the ring-opening reactions of lithium oxetenoxides is not consistent with the bulkiness of substituents, and both the bulkier tert-butyl and silyl substituents favor inward rotation. With the aid of B3LYP calculations, the hyperconjugative interaction between the breaking C 1-O σ and its anti-periplanar Z-Me (Z = Si or C) σ* orbital is found to be responsible among the secondary orbital interactions of the substituents and the oxetene moiety.

Original languageEnglish
Pages (from-to)3945-3948
Number of pages4
JournalOrganic letters
Issue number22
Publication statusPublished - Oct 28 2004
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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