STEREOELECTRONIC EFFECTS IN SULFONYL COMPOUNDS - AXIAL ORIENTATION OFAN N-METHYL GROUP IN A 6-MEMBERED SULTAM

Authors
KING JF YUYITUNG G GILL MS STEWART JC PAYNE NC
Citation
Jf. King et al., STEREOELECTRONIC EFFECTS IN SULFONYL COMPOUNDS - AXIAL ORIENTATION OFAN N-METHYL GROUP IN A 6-MEMBERED SULTAM, Canadian journal of chemistry, 76(2), 1998, pp. 164-170
Citations number
31
Categorie Soggetti
Chemistry
Journal title
Canadian journal of chemistry → ACNP
ISSN journal
00084042
Volume
76
Issue
2
Year of publication
1998
Pages
164 - 170
Database
ISI
SICI code
0008-4042(1998)76:2<164:SEISC->2.0.ZU;2-H
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, ha s been synthesized. The single-crystal X-ray structure shows the molec ule to have the N-methyl group in the axial orientation. The generaliz ed anomeric effect believed to be responsible for the axial preference is estimated at greater than or equal to 2 kcal mol(-1).