Gold(III) halides catalyze the oxidation of sulfides to sulfoxides in a phase-transfer process. The organic sulfides, dissolved in nitromethane, are treated with (Bu4N+AuCl4-) in catalytic amount and aqueous nitric acid which acts as oxidant. The oxidation of the thio-group is selective and can be carried out also in the presence of other oxidizable groups, such as vinyl, tertiary amino, hydroxy, diol etc, which are left unchanged. Moreover in the case of asymmetric disulfides the reaction is regiospecific leading to the formation of a single monosulfoxide.
Gold(III) catalyzed oxidation of sulfides to sulfoxides by nitric acid under phase-transfer conditions: a new synthesis of sulfoxides / Gasparrini, Francesco; Giovannoli, Mario; Misiti, Domenico; G., Natile; G., Palmieri. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 39:19(1983), pp. 3181-3184. [10.1016/s0040-4020(01)91563-7]
Gold(III) catalyzed oxidation of sulfides to sulfoxides by nitric acid under phase-transfer conditions: a new synthesis of sulfoxides
GASPARRINI, Francesco;GIOVANNOLI, Mario;MISITI, Domenico;
1983
Abstract
Gold(III) halides catalyze the oxidation of sulfides to sulfoxides in a phase-transfer process. The organic sulfides, dissolved in nitromethane, are treated with (Bu4N+AuCl4-) in catalytic amount and aqueous nitric acid which acts as oxidant. The oxidation of the thio-group is selective and can be carried out also in the presence of other oxidizable groups, such as vinyl, tertiary amino, hydroxy, diol etc, which are left unchanged. Moreover in the case of asymmetric disulfides the reaction is regiospecific leading to the formation of a single monosulfoxide.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
