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Boron‐Nitrogen Compounds. 88 [1]. Boron Derivatives of Pyridylalkylamines
Author(s) -
Niedenzu K.,
Read R. B.
Publication year - 1981
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.19814730216
Subject(s) - chemistry , medicinal chemistry , pyridine , boron , methylamine , yield (engineering) , intramolecular force , trimethylamine , bicyclic molecule , reactivity (psychology) , stereochemistry , organic chemistry , materials science , medicine , alternative medicine , pathology , metallurgy
2‐Aminomethylpyridine and 2‐aminoethylpyridine, when reacted in a 1:2 molar ratio with trialkylboranes, form intermediates which on pyrolysis yield (2‐pyridylalkylamino)dialkylboranes, C 5 H 4 N2‐(CH 2 ) n NHBR 2 (n = 1 or 2; R = C 2 H 5 , n‐C 3 H 7 ). Nuclear magnetic resonance data show that if R = C 2 H 5 the compounds exist in an intramolecular coordinated bicyclic structure containing four‐coordinate boron. If R = C 3 H 7 , the species with n = 1 exists in both the noncoordinated (with trigonal boron) as well as the bicyclic coordinated form, but with n = 2 the compound exists exclusively in the open form with trigonal boron. — The two cited bases are similar in their reactivity with tetracoordinated boron derivatives. With trimethylamine‐borane, both amines undergo identical simultaneous base displacement and condensation to yield amine‐aminoboranes, 2‐[H 2 BNH(CH 2 ) n ]C 5 H 4 NBH 3 , while in the case of trimethylamine‐iodoborane base displacement and iodide ion displacement occurs with either pyridine derivative to yield a boronium(1+) salt.