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Reactivity of Dithiazinanes towards BH 3 , BD 3 and BF 3 . 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‐5azonia‐4‐boratacyclohexane. A Method for the Dimethylation and Monodeuteriomethylation of Primary Amines
Author(s) -
FloresParra Angelina,
CadenasPliego Gregorio,
MartínezAguilera Luz Maria R.,
Lourdes GarcíaNares M.,
Contreas Rosalinda
Publication year - 1993
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.19931260403
Subject(s) - chemistry , borane , adduct , yield (engineering) , reactivity (psychology) , medicinal chemistry , boron , amine gas treating , primary (astronomy) , stereochemistry , organic chemistry , catalysis , medicine , materials science , alternative medicine , physics , pathology , astronomy , metallurgy
5‐Methyl‐and 5‐ tert 1‐butyl‐1,3,5‐dithiazinane ( 1 and 7 ) react with BH 3 ·THF, and Et 2 O·BF 3 to yield the N 1‐coordinated adducts 2 – 4 (with BH 3 , BD 3 , and BF 3 , respectively). The conformations and spectroscopic properties of the adducts are discussed. The reactions of 1 and 7 with BY 3 ·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[D 1 ]methyl‐1,3‐dithia‐5‐azonia‐4‐boratacyclohexane ( 6 ), and 5‐ tert 1‐butyl‐5‐methyl‐1,3‐dithia‐5‐azonia‐4‐boratacy‐clohexane ( 8 ). Compounds 2 and 5 are isolobal isomers. The reaction of BH 3 or BD 3 with 7 affords, after heating, tert 1‐butyldimethylamine – borane ( 9 ) and tert 1‐butyldi([D 1 ]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.