Molecules 2002, 7(10), 721-733; doi:10.3390/71000721
Article

Different Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate

Min Shi* email, Chao-Qun Li and Jian-Kang Jiang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 China
* Author to whom correspondence should be addressed.
Received: 27 August 2002; in revised form: 10 October 2002 / Accepted: 11 October 2002 / Published: 31 October 2002
PDF Full-text Download PDF Full-Text [61 KB, uploaded 3 October 2008 11:35 CEST]
Abstract: In the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone we have observed exclusive formation of diadducts 4, and that the yields of diadduct can reach 80% with increasing amounts of phenyl vinyl ketone. On the other hand, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The effects of substituents were also examined and a plausible reaction mechanism is proposed for the formation of compounds 4.
Keywords: Baylis-Hillman reaction; Lewis base; Phenyl vinyl ketone (PVK); Phenyl acrylate; DABCO; Conjugate addition; DMAP

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

Shi, M.; Li, C.-Q.; Jiang, J.-K. Different Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate. Molecules 2002, 7, 721-733.

AMA Style

Shi M, Li C-Q, Jiang J-K. Different Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate. Molecules. 2002; 7(10):721-733.

Chicago/Turabian Style

Shi, Min; Li, Chao-Qun; Jiang, Jian-Kang. 2002. "Different Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate." Molecules 7, no. 10: 721-733.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert