Reaction of N,N-dialkyl-N-(trimethylsilyl)methyl-γ-substituted allylammonium salts with cesium fluoride

Chen Zhang; Yasuhiro Maeda; Yoshiro Sato

doi:10.1248/cpb.46.572

Reaction of N,N-dialkyl-N-(trimethylsilyl)methyl-γ-substituted allylammonium salts with cesium fluoride

Chen Zhang
, Yasuhiro Maeda
, Yoshiro Sato

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

The reaction of N,N-dialkyl-N-(trimethylsilyl)methyl-γ- (methoxycarbonyl or cyano)allylammonium salts (1e, g, h) with cesium fluoride in N,N-dimethylformamide (DMF) did not form the expected allyl rearrangement products 3 of N-methylides 2, and instead gave N,N-dialkyl-3-(methoxycarbonyl or cyano)-2-(fluoromethyl)propylamines (9e, g, h) as the main product. The reaction mechanism is discussed.

Original language	English
Pages (from-to)	572-576
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	46
Issue number	4
DOIs	https://doi.org/10.1248/cpb.46.572
Publication status	Published - 1998
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry
Drug Discovery

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10.1248/cpb.46.572

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author = "Chen Zhang and Yasuhiro Maeda and Yoshiro Sato",

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AU - Zhang, Chen

AU - Maeda, Yasuhiro

AU - Sato, Yoshiro

PY - 1998

Y1 - 1998

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AB - The reaction of N,N-dialkyl-N-(trimethylsilyl)methyl-γ- (methoxycarbonyl or cyano)allylammonium salts (1e, g, h) with cesium fluoride in N,N-dimethylformamide (DMF) did not form the expected allyl rearrangement products 3 of N-methylides 2, and instead gave N,N-dialkyl-3-(methoxycarbonyl or cyano)-2-(fluoromethyl)propylamines (9e, g, h) as the main product. The reaction mechanism is discussed.

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UR - https://www.scopus.com/pages/publications/0031968309#tab=citedBy

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ER -

Reaction of N,N-dialkyl-N-(trimethylsilyl)methyl-γ-substituted allylammonium salts with cesium fluoride

Abstract

All Science Journal Classification (ASJC) codes

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