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, Akira

Matsuoka, Yoshiyuki

Suzuki, Yumiko

Iwamoto, Ken-Ichi

Higashino, 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).

Full text of DOI:10.1248/cpb.45.1235

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