Reaction of α‐lithio O‐alkyloximes with diiodomethane – a synthesis of α‐iodomethylene oxime ethers

Shimon Shatzmiller*, Ramy Lidor, Eliezer Babar

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Regiocontrolled deprotonation (e. g. lithiation) of acetone O‐methyloxime (1), 5,6‐dihydro‐3‐methyl‐4H‐1,2‐oxazine (9a) and 4,5‐dihydro‐3‐methylisoxazole (9b) is achieved within 1 minute at −65°C in hexane/THF. The lithiated compounds react very fast at low temperature (−65°C) with diidomethane to give mainly the corresponding α‐iodomethylene oxime ethers 6 and 11a, b. A radical mechanism of this reaction is discussed.

Original languageEnglish
Pages (from-to)381-383
Number of pages3
JournalLiebigs Annalen der Chemie
Volume1991
Issue number4
DOIs
StatePublished - 1991

Keywords

  • 1‐Azabutadiene
  • Iodomethylene oxime ethers
  • Oxime ethers

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