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1. Stereoelectronic effects in sulfonyl compounds: axial orientation of an N-methyl group in a six-membered sultam

Author

James Frederick King, Gay Yuyitung, Manjinder Singh Gill, Jeffrey Charles Stewart, and Nicholas Charles Payne

Subjects
Sulfonyl, chemistry.chemical_classification, chemistry.chemical_compound, Anomeric effect, Cyclohexane, chemistry, Stereochemistry, Organic Chemistry, General Chemistry, Catalysis, Methyl group
Abstract

The trans form of octahydro-1-methyl-1H-2,1-benzothiazine 2,2-dioxide, in which a six-membered sultam unit is trans-fused to cyclohexane, has been synthesized. The single-crystal X-ray structure shows the molecule to have the N-methyl group in the axial orientation. The generalized anomeric effect believed to be responsible for the axial preference is estimated at =>2 kcal mol-1.Key words: generalized anomeric effect, negative hyperconjugation, sulfonamides, sultams, X-ray crystallography.

Published
1998
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