Thiirane tetraphenyl

Thermolysis of allene 329 with diphenyldiazomethane in benzene afforded 3-benzylthio-l,3,4,4-tetraphenyl-l-butyne 330 and 2,2,3,3-tetraphenylthiirane 331 in 11% and 87% yields, respectively. Thermolysis of bicyclic allene 332 with diphenyldiazomethane under the same conditions as above gave a mixture of thiirane 331, compound 332, 1,3-dithiolane 334, and tricyclic 335 in 12%, 17%, 13%, and 48% yields, respectively (Equations 49 and 50). It was found that heating of a benzene solution of 335 with diphenyldiazomethane gave a mixture of 333 and 334 together with thiirane 331 in 41%, 29%, and 20% yields, respectively <2000JOC1721>. 

The reaction of 2,3-diphenyl- or 2,3-bis-(4-chlorophenyl)-thiiren 1,1-dioxide with enamines R R C=CR NR 2 yields a variety of heterocyclic compounds, including medium- and large-ring sulphur heterocycles, via decomposition of a bicyclic thiiran dioxide intermediate (26). Treatment of these thiiran dioxides with 2-pyrrolidinyl- or 2-piperidinyl-2-norbornene gave adducts which possessed antifertility activity. The reaction of 2,3-diphenylthiiren 1,1-dioxide with several meso-ionic compounds, e.g. (27), gave 2,3,5,6-tetraphenyl-4 -l,4-thiazine 1,1-dioxides by loss of carbon dioxide from the intermediate adduct (28). ... 

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