FORMATION OF DEOXYBENZOINS FROM 1, 3-DIMETHYL-2-(α-BENZYLOXYBENZYL)BENZIMIDAZOLIUM IODIDES THROUGH REARRANGEMENT FOLLOWED BY EXPULSION OF AZOLIUM YLIDE

FORMATION OF DEOXYBENZOINS FROM 1, 3-DIMETHYL-2-(α-BENZYLOXYBENZYL)BENZIMIDAZOLIUM IODIDES THROUGH REARRANGEMENT FOLLOWED BY EXPULSION OF AZOLIUM YLIDE

Treatment of several 1, 3-dimethyl-2-(α-benzyloxybenzyl)benzimidazolium iodides 1 with K2CO3 gave deoxybenzoins 2 in moderate yields. Deoxybenzoins 2 were produced through rearrangement of benzyl groups followed by expulsion of 1, 3-dimethylbenzimidazolium ylide (4). The reaction is classified as a...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1994/09/15, Vol.42(9), pp.1960-1962
Hauptverfasser: MIYASHITA, Akira, MATSUOKA, Yoshiyuki, IWAMOTO, Ken-ichi, HIGASHINO, Takeo
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Sprache:eng
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1, 3-dimethyl-2-(α-banzyloxybenzyl)benzimidazolium iodide
1, 3-dimethylbenzimidazolium ylide
deoxybenzoin
elimination
rearrangement
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container_end_page 1962
container_issue 9
container_start_page 1960
container_title Chemical & pharmaceutical bulletin
container_volume 42
creator MIYASHITA, Akira
MATSUOKA, Yoshiyuki
IWAMOTO, Ken-ichi
HIGASHINO, Takeo
description Treatment of several 1, 3-dimethyl-2-(α-benzyloxybenzyl)benzimidazolium iodides 1 with K2CO3 gave deoxybenzoins 2 in moderate yields. Deoxybenzoins 2 were produced through rearrangement of benzyl groups followed by expulsion of 1, 3-dimethylbenzimidazolium ylide (4). The reaction is classified as a Witting rearrangement.
doi_str_mv 10.1248/cpb.42.1960
format Article
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ispartof Chemical and Pharmaceutical Bulletin, 1994/09/15, Vol.42(9), pp.1960-1962
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subjects 1, 3-dimethyl-2-(α-banzyloxybenzyl)benzimidazolium iodide
1, 3-dimethylbenzimidazolium ylide
deoxybenzoin
elimination
rearrangement
title FORMATION OF DEOXYBENZOINS FROM 1, 3-DIMETHYL-2-(α-BENZYLOXYBENZYL)BENZIMIDAZOLIUM IODIDES THROUGH REARRANGEMENT FOLLOWED BY EXPULSION OF AZOLIUM YLIDE
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