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Dedicated with warm regards to Professor Gurnos AbstractTetrasulfur tetranitride 1 reacts with phenyl vinyl sulfoxide 3 or sulfone or phenyl vinyl sulfonate to give the planar delocalised 14 P electron aromatic system 1 λ4δ2 , 3,5,7 λ4δ2 -tetrathia-2,4,6,8-tetraza-azulene 4 as stable dark metallic lustrous crystals. All the sulfur and nitrogen atoms of S 4 N 4 have been retained and a C-C P bond incorporated, the 12 P cage structure of S 4 N 4 being converted into the planar bicyclic system. A mechanism is proposed for this transformation. The ability of the vinyl component to act as an acetylene equivalent and to suffer dehydrogenation to give the aromatic product appear to be necessary for this type of reaction since more highly substituted sulfoxides lead only to decomposition. Optimum conditions for the reaction of phenyl vinyl sulfoxide with S 4 N 4 (3.6 equiv.) in refluxing xylene for 7.5 h give the tetrathiatetrazaazulene 4 in 35%.

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New Routes to Benzothiophenes, Isothiazoles and 1,2,3-Dithiazoles.-New and clean conversions of the dithiazolethione (I) into highly functionalized isothiazoles (V), (VI) and benzothiophene (IX) are described. Plausible mechanisms are proposed for all of these reactions.-(EMAYAN, K.; ENGLISH, R. F.; KOUTENTIS, P. A.; REES, C. W.; J.