A Comparative Oxidation Study of Some Thiane Derivatives.

Abstract

(S4bis) , 8-9000 GHENT (Belgium).Received 91 1/77 -Accepted IOl3177. Abstract.Three thianes substituted with a *-a',y'-diMe holding group and with i n the 6-ringposit i o n of sulfur a C-. 0-and S-atom respectively have been oxidized with a v a r i e t y of oxidants and the i s w e r i c d i s t r i b u t i o n s of the r e s u l t i n g mono-sulfoxides have been analyzed by gaschromatography.s t r a i n t s from r i n g substituents and t o the e l e c t r o n i c f e a t u r e s of the s u b s t r a t e molecules.The stereochemistry of these oxidations appears t o be s e n s i t i v e t o s t e r i c con-

Conformationally Constrained Oxides of 1,3‐Dithiane: Synthesis and NMR Spectroscopic Investigations

“…Most of the dimethyldithiane‐derived oxidised compounds were accessible starting from the parent 4,6‐dimethyl‐1,3‐dithiane ( 11 ), which was obtained from meso ‐pentane‐2,4‐diol according to published protocols 22. It has already been noted that the oxidation of 1,3‐dithiane and its derivatives preferentially leads to equatorial sulfoxides, for example, 11 → 13 23. This is in accordance with calculations on the stability of the monosulfoxides: equatorial sulfoxide 3 is 7.8 kJ/mol more stable than the axial sulfoxide 2 (cf.…”

Thione Derivatives as Medicinally Important Compounds

“…[9] However, a number of other sulfur compounds have brought our attention and one of them is thiones. The other sulfur-containing compounds include thienopyrimidines, [10] thiadiazoles, [11] thiazoles, [12] benzothiazoles, [13] thiophenes, [14] thianes [15] etc.…”