Heinemann FW (2007)
Publication Status: Published
Publication Type: Journal article
Publication year: 2007
Publisher: SPRINGER/PLENUM PUBLISHERS
Book Volume: 37
Pages Range: 165-170
Journal Issue: 3
DOI: 10.1007/s10870-006-9177-2
The absolute configuration at the chiral sulfurs centers of (-)-(S (S) , 1R, 2S, 5R)-menthyl-p-tolylsulfinate (1) and (S (S) )-[(p-tolyl)sulfinyl]ferrocene (2) were determined by single crystal X-ray diffraction with anomalous dispersion effects and the corresponding calculation of Flack's absolute structure parameters. Both compounds crystallize in the monoclinic crystal system in space group P2(1) (no. 4); chiral sulfinate ester 1: a = 8.2868(6), b = 6.1399(3), c = 16.366(2) angstrom, beta = 91.816(6)degrees, V = 832.3(2) angstrom(3), Z = 2 and absolute structure parameter -0.03(7); chiral ferrocenyl sulfoxide 2: a = 5.8371(3), b = 15.390(2), c = 16.143(2) angstrom, beta = 97.748(6)degrees, V = 1436.9(3) angstrom(3), Z = 4 and absolute structure parameter +0.01(1). The trigonal pyramidal geometry at the chiral sulfur atom of 2 is close to expected values while the one of 1 is slightly distorted. With direct determination of the absolute configuration at the chiral sulfur centers an important gap concerning the widely used precursors 1 and 2 for the syntheses of chiral sulfoxides and 1,2-disubstituted planar chiral ferrocenyl ligands is now closed. The latter substance class is playing a key role in enantioselective catalysis.
APA:
Heinemann, F.W. (2007). Crystal structures of (-)-(S (S), 1R, 2S, 5R)-menthyl p-tolyl sulfinate and (+)-(S (S) )-[(p-tolyl)sulfinyl]ferrocene. Journal of Chemical Crystallography, 37(3), 165-170. https://doi.org/10.1007/s10870-006-9177-2
MLA:
Heinemann, Frank Wilhelm. "Crystal structures of (-)-(S (S), 1R, 2S, 5R)-menthyl p-tolyl sulfinate and (+)-(S (S) )-[(p-tolyl)sulfinyl]ferrocene." Journal of Chemical Crystallography 37.3 (2007): 165-170.
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