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Esterifications with 2-(Trimethylsilyl)ethyl 2,2,2-Trichloroacetimidate

1-014 Center for Science and Technology, Department of Chemistry, Syracuse University, Syracuse, NY 13244, USA
Author to whom correspondence should be addressed.
Academic Editor: Wim Dehaen
Received: 17 January 2021 / Revised: 25 January 2021 / Accepted: 1 February 2021 / Published: 4 February 2021
(This article belongs to the Special Issue Feature Papers in Organics)
2-(Trimethylsilyl)ethyl 2,2,2-trichloroacetimidate is readily synthesized from 2-trimethylsilylethanol in high yield. This imidate is an effective reagent for the formation of 2-trimethylsilylethyl esters without the need for an exogenous promoter or catalyst, as the carboxylic acid substrate is acidic enough to promote ester formation without an additive. A deuterium labeling study indicated that a β-silyl carbocation intermediate is involved in the transformation. View Full-Text
Keywords: esters; β-silyl carbocations; trichloroacetimidates; protecting groups; C-O bond formation esters; β-silyl carbocations; trichloroacetimidates; protecting groups; C-O bond formation
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MDPI and ACS Style

Lin, W.; Meyer, S.T.; Dormann, S.; Chisholm, J.D. Esterifications with 2-(Trimethylsilyl)ethyl 2,2,2-Trichloroacetimidate. Organics 2021, 2, 17-25.

AMA Style

Lin W, Meyer ST, Dormann S, Chisholm JD. Esterifications with 2-(Trimethylsilyl)ethyl 2,2,2-Trichloroacetimidate. Organics. 2021; 2(1):17-25.

Chicago/Turabian Style

Lin, Wenhong, Shea T. Meyer, Shawn Dormann, and John D. Chisholm 2021. "Esterifications with 2-(Trimethylsilyl)ethyl 2,2,2-Trichloroacetimidate" Organics 2, no. 1: 17-25.

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