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A new method of synthesizing deoxybenzoins from 1,3-dimethyl-2-(α- benzyloxybenzyl)imidazolium and 1,3-dimethyl-2-(α- benzyloxybenzyl)benzimidazolium iodides based on Wittig-type rearrangement

DOI: 10.1248/cpb.45.1235

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1235 - 1242 (1997)

Update date:2022-08-03

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Authors:

Miyashita, AkiraMiyashita, Akira

Matsuoka, YoshiyukiMatsuoka, Yoshiyuki

Suzuki, YumikoSuzuki, Yumiko

Iwamoto, Ken-IchiIwamoto, Ken-Ichi

Higashino, TakeoHigashino, Takeo

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Article abstract of DOI:10.1248/cpb.45.1235

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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Full text of DOI:10.1248/cpb.45.1235

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Product name:1-(1-Methyl-1H-benzoimidazol-2-yl)-1,2-diphenyl-ethanol

Cas No:187336-09-0

187336-09-0

R&D Labs maybe for 187336-09-0

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