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Communication | Regular issue | Vol 22, No. 1, 1984, pp.27-32
Published online, 1st January, 1970
DOI: 10.3987/R-1984-01-0027
Rearrangement of 1,4,2-Benzodithiazines to 2-Imino-1,3-benzodithioles. Its Unprecedented Characteristic Features (An Extreme Case of Solvent Effect)

Juzo Nakayama,* Atsuhiro Sakai, Shoichi Tokita, and Masamatsu Hoshino

*Department of Chemistry, Faculty of Science, Saitama University, Saitama, Saitama 338-8570, Japan

Abstract

3-Unsubstituted 1,4,2-benzodithiarines undergo a new thermal rearrangement to give 2-imino-1,3-benzodithioles. The most characteristic feature of this rearrangement is that it occurs smoothly only when benzodithiazines were heated without solvent, but it does not take place in non-polar solvents. A plausible mechanism of this rearrangement is proposed on the basis of available experimental data.