Hétérobicycles sulfurés dérivés de l'α-thioglycérol. Synthèse d'alkyl-2,8-dioxa-6-thiabicyclo[3.2. 1]octanes

Abstract

The synthesis of 2,8-dioxa-6-thiobicyclo[3.2.1]octanes, substituted by alkyl or phenyl groups in positions 1, 4, or 7, is described. Four synthetic routes are compared: (i) action of sodium sulfide on 2,4-dichloro-1,3-dialkyldioxolanes; (ii) action of sodium sulfide on the ditosylates of 2,4-dihydroxyalkyl-1,3-dioxolanes; (iii) action of α-haloketones on α-thioglycerol; and (iv) action of α-hydroxyketones on α-thioglycerol. The structures of the dioxathiabicyclooctanes have been established by proton nmr (mass spectra have already been described) and chemically confirmed by desulfurization by Raney Nickel. [Journal translation]