The invention of radical reactions. Part XXIII new reactions: Nitrile and thiocyanate transfer to carbon radicals from sulfonyl cyanides and sulfonyl isothiocyanates

Article abstract of DOI:10.1016/S0040-4020(01)88524-0

Reaction of p-toluenesulphonyl cyanide or methanesulfonyl cyanide with carbon radicals, generated from the corresponding O-acyl-N-hydroxy-2-thiopyridone derivatives by visible light photolysis gives nitriles in good yield. The homolysis products of these sulfonyl nitriles can also be trapped by electron rich olefins. We have also found that carbon radicals react easily with mesyl or tosyl isothiocyanate producing thiocyanates.