ISSN:
0009-2940
Keywords:
Dithiazinanes
;
Dithiazoniaboratacyclohexane
;
Amines: dimethylation and monodeuteriomethylation
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
5-Methyl-and 5-tert1-butyl-1,3,5-dithiazinane (1 and 7) react with BH3·THF, and Et2O·BF3 to yield the N1-coordinated adducts 2 - 4 (with BH3, BD3, and BF3, respectively). The conformations and spectroscopic properties of the adducts are discussed. The reactions of 1 and 7 with BY3·THF lead to the six-membered boron heterocycles 5,5-dimethyl-1,3-dithia-5-azonia-4-boratacyclohexane (5), 4,4-dideuterio-5-methyl-5[D1]methyl-1,3-dithia-5-azonia-4-boratacyclohexane (6), and 5-tert1-butyl-5-methyl-1,3-dithia-5-azonia-4-boratacy-clohexane (8). Compounds 2 and 5 are isolobal isomers. The reaction of BH3 or BD3 with 7 affords, after heating, tert1-butyldimethylamine - borane (9) and tert1-butyldi([D1]methyl)1-amine - trideuterioborane (11), respectively. The dithiazinane derivatives may be used in organic synthesis for the dimethylation of primary amines and the preparation of alkyldimethylamines with monodeuterated methyl groups.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260403
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