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Beiträge zur Chemie des Bors, 199 Reaktionen eines Amino‐imino‐borans mit Anilin‐Derivaten und Carbonsäureamiden
Author(s) -
Brandl Andreas,
Geisberger Gilbert,
Nöth Heinrich
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230112
Subject(s) - chemistry , borane , acetamide , steric effects , aniline , medicinal chemistry , boranes , yield (engineering) , substituent , stereochemistry , organic chemistry , boron , catalysis , materials science , metallurgy
Contributions to the Chemistry of Boron, 199. ‐ Reactions of an Amino‐imino‐borane with Anilines and Carboxylic Acid Amides The addition of aniline derivatives to ( tert ‐butylimino)(2,2,6,6‐tetramethylpiperidino)borane ( 1 ) leading to the mixed triaminoboranes ArNH(Me 3 CNH)Btmp ( 2 ) (tmp = 2,2,6,6‐tetramethylpiperidino) is sterically controlled. Reactions of 1 with acetamide produces O,N ‐diborylated acetimidic acid 4 . On the other hand, N ‐methylacetamide adds 1 to yield the N ‐borylated N ‐methylacetamide 5a exclusively. In contrast, N ‐isopropyl‐ and N‐tert ‐butylacetamide form also the O ‐borated isomers ( 6b, c ). Their proportion increases with the steric requirements of the N ‐substituent of the acetamide derivative.