Stereochemistry of seven-membered heterocycles: XLI. Stereoselective synthesis of 3-R-1,5-dihydro-2,4-benzothiepine 2-oxides

Authors
Kikilo, PA Khairutdinov, BI Shaikhutdinov, RA Shtyrlin, YG Klochkov, VV Klimovitskii, EN
Citation
Pa. Kikilo et al., Stereochemistry of seven-membered heterocycles: XLI. Stereoselective synthesis of 3-R-1,5-dihydro-2,4-benzothiepine 2-oxides, RUSS J G CH, 71(6), 2001, pp. 960-964
Citations number
13
Categorie Soggetti
Chemistry
Journal title
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
ISSN journal
10703632 → ACNP
Volume
71
Issue
6
Year of publication
2001
Pages
960 - 964
Database
ISI
SICI code
1070-3632(200106)71:6<960:SOSHXS>2.0.ZU;2-R
Abstract
The oxidation of 3-R-1,5-dihydro-2,4-benzothiepines with m-chloroperbenzoic acid occurs in a highly diastereoselective fashion. The resulting trans-su lfoxides at -60 degreesC in CDCl3 exist as an equilibrium mixture of the ch air and boat forms with the substituents in the equatorial position. The fr action of the boat conformation increases in the series R = Ph, Me, t-Bu.