Chemical and Pharmaceutical Bulletin p. 1235 - 1242 (1997)
Update date:2022-08-03
Topics:
Miyashita, Akira
Matsuoka, Yoshiyuki
Suzuki, Yumiko
Iwamoto, Ken-Ichi
Higashino, Takeo
The treatment of 1,3-dimethyl-2-(α-benzyloxybenzyl)benzimidazolium iodides 1 with a base gave deoxybenzoins 2 in moderate yields. Sodium hydride (NaH), potassium carbonate (K2CO3), and cesium carbonate (Cs2CO3) were effective bases in this reaction. Deoxybenzoins 2 were produced through rearrangement of the benzyl group followed by expulsion of the 1,3- dimethylbenzimidazolium ylide (A). The rearrangement proceeds in a way similar to Wittig rearrangement. Deoxybenzoins 2 were also formed in good yields from 1,3-dimethyl-2-(α-benzyloxybenzyl)imidazolium iodides 4 upon similar treatment. However, the quaternary salts having a thiazolium moiety 5a and a pyridinium moiety 6a failed to produce deoxybenzoin (2a).
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Doi:10.1080/07328319808004216
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(2002)Doi:10.1055/s-2006-942489
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(1997)
