Absolute configuration, predominant conformations, and vibrational circular dichroism spectra of enantiomers of n-butyl tert-butyl sulfoxide.
Alkylation of the alpha-carbanion of (R)-(-)-tert-butyl methyl sulfoxide (4) with n-propyl bromide afforded (+)-n-butyl tert-butyl sulfoxide (1) to which the absolute configuration (R) was ascribed. This assignment was confirmed by X-ray analysis of the complex 6 obtained from the enantiomerically pure sulfoxide (-)-1 and mercury chloride. Vibrational absorption and circular dichroism spectra of (+)-1 were measured in CDCl3 solution in the 2000-900 cm(-1) region and compared with the ab initio predictions of absorption and VCD spectra obtained with density functional theory using the B3LYP/6-31G basis set for different conformers of (R)-1. This comparison indicated also that (+)-1 is of the (R)-configuration.
Drabowicz
J
J
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Lódz, Sienkiewicza 112, Poland. draj@bilbo.cbmm.lodz.pl
Dudziński
B
B
Mikołajczyk
M
M
Wang
F
F
Dehlavi
A
A
Goring
J
J
Park
M
M
Rizzo
C J
CJ
Polavarapu
P L
PL
Biscarini
P
P
Wieczorek
M W
MW
Majzner
W R
WR