Journal of Organic Chemistry p. 2066 - 2073 (1985)
Update date:2022-08-04
Topics:
Abramovitch, Rudolph A.
Kress, Albert O.
Pillay, Kutten S.
Thompson, W. Marshall
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.
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