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
Format: Artikel
Sprache:eng
Schlagworte:
1, 3-dimethyl-2-(α-banzyloxybenzyl)benzimidazolium iodide
1, 3-dimethylbenzimidazolium ylide
deoxybenzoin
elimination
rearrangement
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Zusammenfassung: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.42.1960