Next Article in Journal
RACI Natural Products Group Symposium
Previous Article in Journal
Regiospecific and Enantiospecific Ring Opening of Methyl (+)-(1'R, 2R)- and (-)-(1'R, 2S)-1-(2-phenylethanol) Aziridine-2-carboxylates
Molecules 2001, 6(11), 852-868; doi:10.3390/61100852
Article

Amine and Titanium (IV) Chloride, Boron (III) Chloride or Zirconium (IV) Chloride-Promoted Baylis-Hillman Reactions

* ,  and
Received: 27 April 2001 / Revised: 11 October 2001 / Accepted: 18 October 2001 / Published: 31 October 2001
Download PDF [95 KB, uploaded 18 June 2014]

Abstract

The Baylis-Hillman reactions of various aryl aldehydes with methyl vinyl ketone at temperatures below -20oC using Lewis acids such as titanium (IV) chloride, boron (III) chloride or zirconium (IV) chloride in the presence of a catalytic amount of selected amines used as a Lewis bases afford the chlorinated compounds 1 as the major product in very high yields. Acrylonitrile can also undergo the same reaction to give the corresponding chlorinated product in moderate yield. A plausible reaction mechanism is proposed. However, if the reaction was carried out at room temperature (ca. 20oC), then the Z-configuration of the elimination product 3, derived from 1, was formed as the major product.
Keywords: Titanium (IV) chloride; boron (III) chloride; zirconium (IV) chloride; Bayliss-Hillman reaction; halogenation; Lewis base; amine Titanium (IV) chloride; boron (III) chloride; zirconium (IV) chloride; Bayliss-Hillman reaction; halogenation; Lewis base; amine
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

Shi, M.; Jiang, J.-K.; Cui, S.-C. Amine and Titanium (IV) Chloride, Boron (III) Chloride or Zirconium (IV) Chloride-Promoted Baylis-Hillman Reactions. Molecules 2001, 6, 852-868.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert