Reactions of lithium salts of O‐alkyl oximes with halogens: A highly stereoselective oxidative coupling of 5,6‐dihydro‐3‐methyl‐4H‐1,2‐oxazine

Shimon Shatzmiller, Ramy Lidor, Eliezer Bahar, Israel Goldberg

Research output: Contribution to journalArticlepeer-review

Abstract

Lithiation of 5,6‐dihydro‐3‐methyl‐4H‐1,2‐oxazine (4) in an unpolar solvent system (hexane/THF) at −65°C followed by reaction with Cl2,Br2, or I2 affords cleanly and stereoselectively 6 (RS,RS) of which an X‐ray structure analysis is described. In contrast, attempts to couple the halogenated 1,2‐oxazine derivative 5c have given, under various reaction conditions, equal amouts of 6 and 8 (meso). A mechanism of this reaction is discussed.

Original languageEnglish
Pages (from-to)851-856
Number of pages6
JournalLiebigs Annalen der Chemie
Volume1991
Issue number9
DOIs
StatePublished - 1991

Keywords

  • 4H‐1,2‐Oxazines
  • Coupling, oxidative
  • Oxime ethers

Fingerprint

Dive into the research topics of 'Reactions of lithium salts of O‐alkyl oximes with halogens: A highly stereoselective oxidative coupling of 5,6‐dihydro‐3‐methyl‐4H‐1,2‐oxazine'. Together they form a unique fingerprint.

Cite this