REACTIVITY OF DIATHIAZINANES TOWARDS BH3, BD3 AND BF3 - NEW HETEROCYCLES - 5,5-DIMETHYL-1,3-DITHIA-5-AZONIA-4-BORATACYCLOHEXANE AND 6,6-DIDEUTERIO-5-METHYL-5-[D(1)]METHYL-1,3-DITHIA-5-AZONIA-4-BORATACYCLOHEXANE - A METHOD FOR THE DIMETHYLATION AND MONODEUTERIOMETHYLATION OF PRIMARY AMINES

5-Methyl- and 5-tert-butyl-1,3,5-dithiazinane (1 and 7) react with BH3 . THF, BD3 . THF, and Et2O . BF3 to yield the N-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-tert-butyl-5-methyl-1,3-dithia-5-azonia-4-boratacyclohexane (8). Compounds 2 and 5 are isolobal isomers. The reaction of BH3 or BD3 With 7 affords, after heating, tert-butyldimethylamine-borane (9) and tert-butyldi([D1]methyl)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.