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P(MeNCH2CH2)3N:  An Efficient Catalyst for the Desilylation of tert-Butyldimethylsilyl Ethers

Zhengkun Yu* and John G. Verkade

*Department of Chemistry, Iowa State University, Ames, Iowa 50011, Email: zkyudicp.ac.cn

Z. Yu, J. G. Verkade, J. Org. Chem., 2000, 65, 2065-2068.

DOI: 10.1021/jo991591i (free Supporting Information)


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Abstract

tert-Butyldimethylsilyl (TBDMS) ethers of primary, secondary, and tertiary alcohols and phenolic TBDMS ethers are desilylated to their corresponding alcohols and phenols, respectively, in DMSO, at 80C, in very good yield in the presence of P(MeNCH2CH2)3N as catalyst. Desilylations of tert-butyldiphenylsilyl (TBDPS) ethers were much less effective.

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proposed mechanism



Nonionic Superbase-Catalyzed Silylation of Alcohols

B. A. D'Sa, D. McLeod, J. G. Verkade, J. Org. Chem., 1997, 62, 5057-5061.


Key Words

TBDMS Ethers, organocatalysis


ID: J42-Y2000