PPh3-Catalyzed Reactions of Alkyl Propiolates withN-Tosylimines: A Facile Synthesis of Alkyl 2-[aryl(tosylimino)methyl]acrylate and an Insight into the Reaction Mechanism

Autor:	Huimin Liu, Limin Wang, Qiongmei Zhang, Xiaofeng Tong
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Reaction mechanism Aryl Organic Chemistry Hydrogen transfer General Chemistry Combinatorial chemistry Catalysis chemistry.chemical_compound chemistry Catalytic cycle Zwitterion Organic chemistry Methyl acrylate Alkyl
Zdroj:	Chemistry - A European Journal. 16:1968-1972
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.200902105
Popis:	A new PPh(3)-catalyzed synthesis of alkyl 2-[aryl(tosylimino)methyl]acrylates from propiolate and N-tosylimine has been developed. Deuterium-labelling experiments show that the reaction mechanism involves several hydrogen-transfer processes, which are not the turnover-limiting step and strongly rely on the nature of the reaction media. The stable phosphonium-enamine zwitterion, which was proven to play an important role in the catalytic cycle, has been isolated and characterised by X-ray analysis.
Databáze:	OpenAIRE
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