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

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
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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

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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.

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