PHOTODECOMPOSITION OF DIANIONS OF DI-P-TOSYLHYDRAZONES OF BIACETYL AND BENZIL

Irradiation of biacetyl di-p-tosylhydrazone dianion through Vycor gives 2-butyne as the only volatile product. The formation of 2-butyne is shown to arise via intermediate formation of the anion of 4,5-dimethyl-1-toluene-p-sulfonamido-1,2,3-triazole, which was isolable in the acid form in 81% yield when the irradiation was carried out employing a Corex filter. Irradiation of benzil di-p-tosylhydrazone dianion through Vycor gave a 74% yield of cis- and trans-α-methoxystilbene formed in the ratio 38:62. 4,5-Diphenyl-1-toluene-p-sulfonamido-1,2,3-triazole was isolated in 25% yield when the irradiation was carried out employing a Corex filter. © 1969, American Chemical Society. All rights reserved.