Abstract: | A synthetically useful C? C bond formation involving the photochemical addition of quinoxaline-2(1H)-thiones to alkenes is described. Irradiation of the quinoxaline-2(1H)-thiones 1–4 in the presence of the alkenes 7 gave the 2-(2′-mercaptoalkyl)quinoxalines 8–11 in moderate-to-good yields via ring cleavage of an intermediate aminothietane with aromatization of the quinoxaline ring. The latter was formed by 2+2] photocycloaddition of the C?S bond of the quinoxaline-2(1H)-thione and the C?C bond of the alkene. |