Rearrangement and Cyclization of β‐Mesyloxy Ketones. Synthesis of δ‐Sultones

Norbert De Kimpe, Marc Boeykens, Laszio Lazar, Z. Szakonyi, Andrejs Kemme, Gunars Duburs

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The reactivity of β‐mesyloxy ketones towards N‐nucleophiles and bases was evaluated. In the presence of titanium(IV) chloride, the reaction with primary amines leads to the formation of β‐mesyloxy imines and β‐amino imines. Upon base treatment, β‐mesyloxy ketones underwent cyclization to δ‐sultones. Increasing steric hindrance in β‐mesyloxy ketones changed the reaction course and gave rise to the formation of cyclobutanones and 2‐methyleneoxetanes.

Original languageEnglish
Pages (from-to)299-302
Number of pages4
JournalBulletin des Sociétés Chimiques Belges
Volume103
Issue number5-6
DOIs
Publication statusPublished - 1994

    Fingerprint

ASJC Scopus subject areas

  • Chemistry(all)

Cite this