ISSN:
0009-2940
Keywords:
Nitriles
;
Hydroboration
;
Bis(9H-9-borabicyclo[3.3.1]nonane)
;
N-Base-Organoboron adducts
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The hydroboration of benzo-, tolu-, p1-methoxybenzo-, or pivalonitriles with bis(9-borabicyclo[3.3.1]nonane) (9H-9-BBN)2 affords the corresponding 9-aldimino-9-borabicyclo[3.3.1]1-nonanes (1a - d) in about 80% yields. Compounds 1a and 1d readily react with an excess of (9H-9-BBN)2 to form the 1:1 adducts 2a or 2d, respectively, containing a NB2H four-membered ring (X-ray structure of 2a). The adducts 2 are thermally rather stable. Compound 2a is converted to benzylbis(1,5-cyclooctanediylboryl)amine (3a) only after 48 h at reflux in mesitylene. Compounds 1a - d are stable towards strong N-bases. Compound 1d reacts with Et2O · BF3 to form 9-fluoro-9-borabicyclo[3.3.1]nonane (4) and the 1:1 cyclic adduct (5d) of (2,2-dimethylpropylideneamino)difluoroborane (6d) and 1d.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260203
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