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

7 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

Access to Document

10.1021/jo00104a055

Cite this

@article{638729fa42fa45018cd6877ad47bcecd,

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",

publisher = "American Chemical Society",

number = "25",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/3643110672

UR - https://www.scopus.com/pages/publications/3643110672#tab=citedBy

U2 - 10.1021/jo00104a055

DO - 10.1021/jo00104a055

M3 - Article

AN - SCOPUS:3643110672

SN - 0022-3263

VL - 59

SP - 7897

EP - 7901

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

Rearrangement of (Polymethoxybenzyl)ammonium N-Methylides

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this