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1 H n.m.r. study and conformation of 3,3‐dimethyl‐3‐sila‐1‐heterocyclohexanes and derivatives (heteroatom SiCl 2 , SiMe 2 , O, NMe, S, Se, Te)
Author(s) -
Anteunis Marc J. O.,
Dedeyne Raymond
Publication year - 1977
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270090304
Subject(s) - heteroatom , chemistry , cyclohexane , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry
It is found that the basic form of the 3,3‐dimethyl‐3‐sila‐1‐heterocyclohexane family (heteroatom X = O, NMe, S, Se, Te, SiMe 2 , SiCl 2 ) is the chair, having ring torsion angles in the aliphatic region tending to be somewhat more puckered (up to 7°) than in cyclohexane, except next to Si when the other heteroatom is relatively small. The 5‐tertiarybutyl‐, 6‐methyl‐ and 2‐phenyl derivatives are all anancomeric, except for the latter two derivatives when X = NMe. A 5‐tertiarybutyl group causes an additional deformation, e.g. an increased puckering of the aliphatic C‐4C‐5C‐6 region (buttressing effect). Other 1 H n.m.r. features are discussed in detail, and the behaviour of the 3‐sila‐1‐heterocyclohexanes is compared with other 1,3‐diheterocyclohexanes.