Abstract
Thermolysis, at ca. 110 °C, of the strained norbornane furazan N-oxides (5)–(8) in toluene, saturated with sulphur dioxide, affords the isomeric 1,3-di-isocyantocyclopentanes (14)–(17). Product formation is explained by a mechanism involving cleavage of the furazan ring to cyclopentane-1,3- bis(nitrile oxides)[e.g.(9)], followed by 1,3-dipolar cycloaddition with SO2 to form bis-1,3,2,4-dioxathiazol-2-ones [e.g.(12)]. Subsequent extrusion of SO2 and rearrangement yields di-isocyanates [e.g.(14)] which were identified spectroscopically and by preparation of urethane and/or urea derivatives on reaction with alcohols and aniline. Compound (8) with aniline gives the cyclic biuret (20) rather than a bis-urea, the structure of the product being established by X-ray crystallography. In the absence of SO2 polymeric furoxans are formed.
Published Version
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