Solution and Flash Vacuum Pyrolysis of Some 2,6-Disubstituted β-Phenethylsulfonyl Azides and of β-Styrenesulfonyl Azide

Article abstract of DOI:10.1021/jo00212a013

Solution thermolysis of 2,6-dichloro-β-phenethyl- and 2,6-dimethyl-β-phenethylsulfonyl azide leads to the formation of the corresponding 5,8-disubstituted 3,4-dihydro-2,1-benzothiazine 2,2-dioxides resulting from a 1,2-chlorine and -methyl shift, respectively, in the intermediates.No insertion into the phenethyl side chain, or into the side-chain methyl group in the 2,6-dimethyl case, was detected.Attempted cyclization of ethene-sulfonanilides to 2,1-benzothiazine 2,2-dioxide failed.The orientation of the dichlorosultam was established unambiguously by its FVP to 4,7-dichloroindoline and by the synthesis of an authentic sample.Solution thermolysis of β-styrenesulfonyl azide gave only hydrogen abstraction (32) and solvent insertion (33) products, but FVP gave indole, phenylacetonitrile, and phenylacetylene.