Rearrangement of (Polymethoxybenzyl)ammonium N-Methylides

Yasuhiro Maeda; Naohiro Shirai; Yoshiro Sato; Hiroshi Tatewaki

doi:10.1021/jo00104a055

Rearrangement of (Polymethoxybenzyl)ammonium N-Methylides

Yasuhiro Maeda, Naohiro Shirai, Yoshiro Sato, Hiroshi Tatewaki

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

6 Citations (Scopus)

Abstract

Reaction of N,N-dimethyl-N-[(trimethylsilyl)methyl](polymethoxy-substituted benzyl)ammonium iodides 1a-e with cesium fluoride gave polymethoxy-substituted 5-[(dimethylamino)methyl]-6-methylene-1,3-cyclohexadienes 3 and 5 ([2,3] sigmatropic rearrangement products). However, these were quickly hydrolyzed to polymethoxytoluenes 8 during the aqueous workup. The pathway of the hydrolysis of 3 and 5 is discussed.

Original language	English
Pages (from-to)	7897-7901
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	59
Issue number	25
DOIs	https://doi.org/10.1021/jo00104a055
Publication status	Published - 01-12-1994
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00104a055

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title = "Rearrangement of (Polymethoxybenzyl)ammonium N-Methylides",

abstract = "Reaction of N,N-dimethyl-N-[(trimethylsilyl)methyl](polymethoxy-substituted benzyl)ammonium iodides 1a-e with cesium fluoride gave polymethoxy-substituted 5-[(dimethylamino)methyl]-6-methylene-1,3-cyclohexadienes 3 and 5 ([2,3] sigmatropic rearrangement products). However, these were quickly hydrolyzed to polymethoxytoluenes 8 during the aqueous workup. The pathway of the hydrolysis of 3 and 5 is discussed.",

author = "Yasuhiro Maeda and Naohiro Shirai and Yoshiro Sato and Hiroshi Tatewaki",

year = "1994",

month = dec,

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doi = "10.1021/jo00104a055",

language = "English",

volume = "59",

pages = "7897--7901",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Rearrangement of (Polymethoxybenzyl)ammonium N-Methylides

AU - Maeda, Yasuhiro

AU - Shirai, Naohiro

AU - Sato, Yoshiro

AU - Tatewaki, Hiroshi

PY - 1994/12/1

Y1 - 1994/12/1

N2 - Reaction of N,N-dimethyl-N-[(trimethylsilyl)methyl](polymethoxy-substituted benzyl)ammonium iodides 1a-e with cesium fluoride gave polymethoxy-substituted 5-[(dimethylamino)methyl]-6-methylene-1,3-cyclohexadienes 3 and 5 ([2,3] sigmatropic rearrangement products). However, these were quickly hydrolyzed to polymethoxytoluenes 8 during the aqueous workup. The pathway of the hydrolysis of 3 and 5 is discussed.

AB - Reaction of N,N-dimethyl-N-[(trimethylsilyl)methyl](polymethoxy-substituted benzyl)ammonium iodides 1a-e with cesium fluoride gave polymethoxy-substituted 5-[(dimethylamino)methyl]-6-methylene-1,3-cyclohexadienes 3 and 5 ([2,3] sigmatropic rearrangement products). However, these were quickly hydrolyzed to polymethoxytoluenes 8 during the aqueous workup. The pathway of the hydrolysis of 3 and 5 is discussed.

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U2 - 10.1021/jo00104a055

DO - 10.1021/jo00104a055

M3 - Article

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SP - 7897

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

Rearrangement of (Polymethoxybenzyl)ammonium N-Methylides

Abstract

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