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

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

6 被引用数 (Scopus)

抄録

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.

本文言語	英語
ページ（範囲）	7897-7901
ページ数	5
ジャーナル	Journal of Organic Chemistry
巻	59
号	25
DOI	https://doi.org/10.1021/jo00104a055
出版ステータス	出版済み - 01-12-1994
外部発表	はい

All Science Journal Classification (ASJC) codes

有機化学

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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,

day = "1",

doi = "10.1021/jo00104a055",

language = "English",

volume = "59",

pages = "7897--7901",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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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

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

Rearrangement of (Polymethoxybenzyl)ammonium N-Methylides

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