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Atropisomerism in hindered naphthyl sulfoxides: structure, stereodynamics, and chiral resolution

Authors :
Casarini, D.
Foresti, E.
Gasparrini, F.
Lunazzi, L.
Macciantelli, D.
Misiti, D.
Villani, C.
Source :
Journal of Organic Chemistry. Oct 8, 1993, Vol. 58 Issue 21, p5674, 9 p.
Publication Year :
1993

Abstract

Inter-transformation obstacles are seen in atropisomers which can be stereochemically allocated and physically isolated by using variable-temperature dynamic NMR, CD spectroscopy and low-temperature HPLC methods. A Z,E interconversion obstacle is calculated in this study by using 1-naphthyl tert-butyl sulfoxide. The longevity of the E atropisomer is shorter than that of the Z atropisomer. The R-enantiomer is longer than the S-enantiomer with the usage of a chiral stationary phase of SS organization.

Details

ISSN :
00223263
Volume :
58
Issue :
21
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.14635634