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

DOI: 10.1248/cpb.46.572

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 572 - 576 (1998)

Update date:2022-08-02

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Authors:

Zhang, Chen

Maeda, Yasuhiro

Sato, Yoshiro

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Article abstract of DOI:10.1248/cpb.46.572

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.

Full text of DOI:10.1248/cpb.46.572

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