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Publication Note Concerning Molecules 2002, 7, 717-720
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

* ,  and
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 / Revised: 10 October 2002 / Accepted: 11 October 2002 / Published: 31 October 2002
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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 Baylis-Hillman reaction; Lewis base; Phenyl vinyl ketone (PVK); Phenyl acrylate; DABCO; Conjugate addition; DMAP
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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.

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