Photochemical transformations. Part XXXIII. Photolysis of thiobenzoic acid O-esters. Part IV. Photolysis of O-phenethyl thiobenzoate derivatives and the formation of thioketones

An efficient and straightforward approach for accessing thionoesters via palladium-catalyzed C–N cleavage of thioamides

“…In 1973, Barton and co-workers described a thionation route from imidate salt intermediates, involving the use of gaseous and toxic H 2 S in the pyridine solvent (Scheme 2a). 27–29 Afterwards, a notable achievement was the introduction of Lawesson's reagent (LR) used for the conversion of carbonyl into the thiocarbonyl functional group (Scheme 2b). 30–32 Even though this method has wide and practical applications, Lawesson's reagent requires an inert atmosphere along with the generation of excess undesired byproducts.…”

Unexpected photoinduced electron transfer reactions of two glucose thiobenzoates †

“…Barton and co-workers have studied the synthetic applications of thiobenzoate photochemistry. [2][3][4][5][6][7] The elimination of thiobenzoic acid to form an alkene by photochemically induced γ-hydrogen abstraction was demonstrated for a number of systems. With cholesterol the hydrogen abstraction was found to be stereo-and regioselective for the axial allylic hydrogen (Scheme 2).…”