Original reaction of p-nitrobenzyl chloride with aldehydes using tetrakis(dimethylamino)ethylene (TDAE)
✍ Scribed by Gamal Giuglio-Tonolo; Thierry Terme; Maurice Médebielle; Patrice Vanelle
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 91 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A series of disubstituted diarylethanols was prepared in moderate to good yields by reaction of p-nitrobenzyl chloride (1) with various aromatic aldehydes (2-12) in presence of tetrakis(dimethylamino)ethylene (TDAE).
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Tetrakis(dimethylamino)ethylcne (TDAE) was fimnd to be an effective reductant of the 2-(bromodifluoromethyl)benzoxazole 1. The generated 2-(difluoromethyl) benzoxazole anion was trapped with several aldehydes 2-9, under mild conditions, to give the corresponding 2-(difluoromcthyl)benzoxazole alcohol