The oxidation of dithiaalkanes has been carried on in a gold(III) catalyzed phase-transfer process. Using a higher concentration of catalyst and oxidant (procedure A) the bis(benzylthio)alkanes Bz-S-(CH2)-S-Bz (Bz = benzyl) were .Oxidized to the corresponding monosulfoxide when n = 1 and to disulfoxide [bis(benzylsulfinyl)alkanes] when n = 2, 3, 4, 5, and 8. In more diluite conditions (procedure B) high yields of monosulfoxides were obtained also in the case of n = .2 and 3 while the selectivity decreased for n = 4, 5, and 8. The oxidation of asymmetric dithiaalkanes, R-S-(CH2)3-S-R' (RR' = BzPh, BzCy, CyPh; Ph = phenyl, Cy = cyclohexyl), under experimental conditions B was regiospecific leading either to the formation of only one type of monosulfoxide (RR' = BzPh) or to the formation of both types of monosulfoxides but in different yield (RR' = BzCy and CyPh); in all cases the alkylic and less hindered sulfur atom was oxidized in preference.
Selective and regiospecific oxidation of dithiaalkanes in a gold(III) catalyzed phase-transfer process / Gasparrini, Francesco; Giovannoli, Mario; Misiti, Domenico; G., Natile; G., Palmieri. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 40:1(1984), pp. 165-170. [10.1016/0040-4020(84)85115-7]
Selective and regiospecific oxidation of dithiaalkanes in a gold(III) catalyzed phase-transfer process
GASPARRINI, Francesco;GIOVANNOLI, Mario;MISITI, Domenico;
1984
Abstract
The oxidation of dithiaalkanes has been carried on in a gold(III) catalyzed phase-transfer process. Using a higher concentration of catalyst and oxidant (procedure A) the bis(benzylthio)alkanes Bz-S-(CH2)-S-Bz (Bz = benzyl) were .Oxidized to the corresponding monosulfoxide when n = 1 and to disulfoxide [bis(benzylsulfinyl)alkanes] when n = 2, 3, 4, 5, and 8. In more diluite conditions (procedure B) high yields of monosulfoxides were obtained also in the case of n = .2 and 3 while the selectivity decreased for n = 4, 5, and 8. The oxidation of asymmetric dithiaalkanes, R-S-(CH2)3-S-R' (RR' = BzPh, BzCy, CyPh; Ph = phenyl, Cy = cyclohexyl), under experimental conditions B was regiospecific leading either to the formation of only one type of monosulfoxide (RR' = BzPh) or to the formation of both types of monosulfoxides but in different yield (RR' = BzCy and CyPh); in all cases the alkylic and less hindered sulfur atom was oxidized in preference.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.