Prev. Article Next Article Table of Contents

Note

Tandem Oxidation/Halogenation of Aryl Allylic Alcohols under Moffatt−Swern Conditions

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Jiandong Yin, Christina E. Gallis, and John D. Chisholm*

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244 jdchisho@syr.edu

J. Org. Chem., 2007, 72 (18), pp 7054–7057

DOI: 10.1021/jo0711992

Publication Date (Web): August 8, 2007

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

Aryl allylic alcohols are converted to halogenated unsaturated ketones or allylic halides using excess Moffatt−Swern reagent. Electron-poor aromatic rings favor formation of the halogenated ketone, while electron-donating substituents in the ortho or para positions favor formation of the allylic halide. The oxidation/halogenation reaction performs well with both oxalyl chloride and oxalyl bromide, providing access to the corresponding chlorides or bromides, respectively.

View: Full Text HTML | Hi-Res PDF | PDF w/ Links

Citing Articles

View all 2 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Preparation of α-Haloacrylate Derivatives via Dimethyl Sulfoxide-Mediated Selective Dehydrohalogenation
Wei Li, Jianchang Li, Zhao-Kui Wan, Junjun Wu, and Walter Massefski
Organic Letters2007 9 (22), 4607-4610
- Preparation of α-Haloacrylate Derivatives via Dimethyl Sulfoxide-Mediated Selective Dehydrohalogenation
  Wei Li, Jianchang Li, Zhao-Kui Wan, Junjun Wu, and Walter Massefski
  Organic Letters2007 9 (22), 4607-4610
  Dimethyl sulfoxide causes ,-dihalopropanoate derivatives to undergo efficient, selective dehydrohalogenation to form -haloacrylate analogues. A variety of -halo Michael acceptors were prepared in dimethyl sulfoxide under mild, base-free conditions, ...
  Abstract | Full Text HTML | Hi-Res PDF