Generation and reaction of benzylammonium N-methylides with N-cyanomethyl or N-(ethoxycarbonylalkyl) groups

Chen Zhang; Yasuhiro Maeda; Naohiro Shirai; Yoshiro Sato

doi:10.1039/a605337h

Generation and reaction of benzylammonium N-methylides with N-cyanomethyl or N-(ethoxycarbonylalkyl) groups

Chen Zhang, Yasuhiro Maeda, Naohiro Shirai, Yoshiro Sato

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

12 Citations (Scopus)

Abstract

N-Cyanomethyl-, N-ethoxycarbonylmethyl- and N-(3-ethoxycarbonylpropyl)-N-methylbenzylammonium N-methylides 6a,b and 22 have been generated by fluoride ion-induced desilylation of the corresponding N-(trimethylsilylmethyl)benzylammonium salts 5a,b and 21. Sommelet-Hauser 7, 23 and Stevens 8, 24 rearrangement products were obtained from 6a and 22, but not from 6b.

Original language	English
Pages (from-to)	25-28
Number of pages	4
Journal	Journal of the Chemical Society - Perkin Transactions 1
Issue number	1
DOIs	https://doi.org/10.1039/a605337h
Publication status	Published - 07-01-1997
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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abstract = "N-Cyanomethyl-, N-ethoxycarbonylmethyl- and N-(3-ethoxycarbonylpropyl)-N-methylbenzylammonium N-methylides 6a,b and 22 have been generated by fluoride ion-induced desilylation of the corresponding N-(trimethylsilylmethyl)benzylammonium salts 5a,b and 21. Sommelet-Hauser 7, 23 and Stevens 8, 24 rearrangement products were obtained from 6a and 22, but not from 6b.",

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

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T1 - Generation and reaction of benzylammonium N-methylides with N-cyanomethyl or N-(ethoxycarbonylalkyl) groups

AU - Zhang, Chen

AU - Maeda, Yasuhiro

AU - Shirai, Naohiro

AU - Sato, Yoshiro

PY - 1997/1/7

Y1 - 1997/1/7

N2 - N-Cyanomethyl-, N-ethoxycarbonylmethyl- and N-(3-ethoxycarbonylpropyl)-N-methylbenzylammonium N-methylides 6a,b and 22 have been generated by fluoride ion-induced desilylation of the corresponding N-(trimethylsilylmethyl)benzylammonium salts 5a,b and 21. Sommelet-Hauser 7, 23 and Stevens 8, 24 rearrangement products were obtained from 6a and 22, but not from 6b.

AB - N-Cyanomethyl-, N-ethoxycarbonylmethyl- and N-(3-ethoxycarbonylpropyl)-N-methylbenzylammonium N-methylides 6a,b and 22 have been generated by fluoride ion-induced desilylation of the corresponding N-(trimethylsilylmethyl)benzylammonium salts 5a,b and 21. Sommelet-Hauser 7, 23 and Stevens 8, 24 rearrangement products were obtained from 6a and 22, but not from 6b.

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