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Aminohaloborane in organic synthesis. VIII. A one-step synthesis of 2-Aminobenzhydrols from anilines

โœ Scribed by Tatsuo Toyoda; Kazuyuki Sasakura; Tsutomu Sugasawa

Publisher
Elsevier Science
Year
1980
Tongue
French
Weight
202 KB
Volume
21
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

2-Aminobenshydrols were obtained regiospecifically from anilines and benzaldehydes with the aid of phenyldichloroborane and triethylamine via N-anilinophenylchloroborane.

We have recently reported a specifically ortho-directed reaction of secondary aniline8 (la) with mainly aromatic aldehydes to give 2-set-aminobenzhydrols (2) using boron trichloride and 2 triethylamine. However, the similar reaction of primary aniline8 (lb) failed to give mainly aldimine (3) (reaction A). We will report here that the use of phenyldichloroborane3 (4) instead of boron trichloride has removed this defect (reaction B). The isolation of 2-phenyl-

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