Neighboring Group Participation in a Regio- and Stereoselective Chlorination of a Bicyclo[2.2.2]octanone

Research output: Contribution to journalArticle

Abstract

The zinc chloride-mediated acetylation of the optically active silyl enol ether 2a gave the beta-diketone 3a (48%) together with the regio- and stereoselectively chlorinated compound 4 (27%). The yield of 4 increased to 70% by starting from the O-acetyl derivative 2c. The chlorination most likely occurs via neighboring group participation by the endo acetoxy group.

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Subject classification (UKÄ) – MANDATORY

  • Organic Chemistry
Original languageEnglish
Pages (from-to)6947-6951
JournalJournal of Organic Chemistry
Volume61
Issue number20
Publication statusPublished - 1996
Publication categoryResearch
Peer-reviewedYes

Bibliographic note

The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Related research output

Almqvist, F., 1996, Organic Chemistry, Lund University. 85 p.

Research output: ThesisDoctoral Thesis (compilation)

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