The reaction of benzothiazole sulfenamide with (TMS)3SiH: An example of degenerate-branched chain process

The radical initiated reaction of 3 with (TMS)3SiH gave benzylmethylamine and thiosilane 5 as main products together with salt 7 as by-product. The amine obtained in a quantitative yield can arise from two independent routes of (TMS)3Si raidcal attack on 3. The minor attack on the ring affords 2-mercaptobenzothiazole that can act as a catalyst for the major route during the reaction course and then gives the salt 7 with amine. The reaction is a rare example of a radical chain-branching process and the origin of autocatalysis is discussed in some details.