A Tandem Nucleophilic Addition, Defluorination and Destannylation. Stereospecific Synthesis of Trifluoromethylated Alkyl and Aryl Vinyl Ethers

Yanchang Shen; Guoping Wang

doi:10.1055/s-2004-831231

PAPER

A Tandem Nucleophilic Addition, Defluorination and Destannylation. Stereospecific Synthesis of Trifluoromethylated Alkyl and Aryl Vinyl Ethers

Yanchang Shen*, Guoping Wang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China
Fax: +86(21)64166128; e-Mail: shenyc@mail.sioc.ac.cn;

Abstract

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Abstract

A novel tandem reaction, including nucleophilic addition, defluorination and destannylation reactions, has been found and its application to the stereospecific synthesis of trifluorometh-ylated alkyl- and aryl vinyl ethers with exclusive formation of E-isomers in 73-96% yields is reported. An Ad_N -E mechanism for the tandem reaction leading to alkyl- and aryl vinyl ethers is proposed.

Key words

trifluoromethylated alkyl- and aryl vinyl ethers - nucleophilic addition - defluorination - destannylation

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References

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