195730-68-8Relevant academic research and scientific papers
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
Miyashita, Akira,Matsuoka, Yoshiyuki,Suzuki, Yumiko,Iwamoto, Ken-Ichi,Higashino, Takeo
, p. 1235 - 1242 (2007/10/03)
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).
Formation of deoxybenzoins from 1,3-dimethyl-2-(α-benzyloxybenzyl)benzimidazolium iodides through rearrangement followed by expulsion of azolium ylide
Miyashita,Matsuoka,Iwamoto,Higashino
, p. 1960 - 1962 (2007/10/02)
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 Wittig rearrangement.
