Electrostatic effects on the reactions of cyclohexanone oxocarbenium ions

Glen Baghdasarian, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

Abstract

Nucleophilic substitution reactions of 4-substituted cyclohexanone acetals display different selectivities depending upon the electronic nature of the substituent. Alkyl groups favor equatorial positions in the oxocarbenium ions, but alkoxy groups prefer axial conformers. The reactions of acetals with alkoxy groups constrained to either equatorial or axial positions suggest that the presence of an axial alkoxy group distorts the oxocarbenium ion, changing its inherent preferences for facial attack.

Original languageEnglish (US)
Pages (from-to)6851-6858
Number of pages8
JournalJournal of Organic Chemistry
Volume71
Issue number18
DOIs
StatePublished - Sep 1 2006

ASJC Scopus subject areas

  • Organic Chemistry

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