Reaction of α-lithioO-alkyloximes with diiodomethane – a synthesis of α-iodomethylene oxime ethers

✍ Scribed by Shatzmiller, Shimon ;Lidor, Ramy ;Babar, Eliezer

• Book ID: 102368017
• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 283 KB
• Volume: 1991
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199119910166

✦ Synopsis

Abstract

Regiocontrolled deprotonation (e. g. lithiation) of acetone O‐methyloxime (1), 5,6‐dihydro‐3‐methyl‐4__H__‐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.