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

Akira MIYASHITA; Yoshiyuki MATSUOKA; Ken-ichi IWAMOTO; Takeo HIGASHINO

doi:10.1248/cpb.42.1960

Akira MIYASHITA, Yoshiyuki MATSUOKA, Ken-ichi IWAMOTO, Takeo HIGASHINO

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Keywords: 1, 3-dimethyl-2-(α-banzyloxybenzyl)benzimidazolium iodide, rearrangement, elimination, 1, 3-dimethylbenzimidazolium ylide, deoxybenzoin

JOURNAL FREE ACCESS

1994 Volume 42 Issue 9 Pages 1960-1962

DOI https://doi.org/10.1248/cpb.42.1960

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Abstract

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.

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