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

Received: 27 April 2001; in revised form: 11 October 2001 / Accepted: 18 October 2001 / Published: 31 October 2001
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.
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
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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.

AMA 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(11):852-868.

Chicago/Turabian Style

Shi, Min; Jiang, Jian-Kang; Cui, Shi-Cong. 2001. "Amine and Titanium (IV) Chloride, Boron (III) Chloride or Zirconium (IV) Chloride-Promoted Baylis-Hillman Reactions." Molecules 6, no. 11: 852-868.

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