The Reaction of Vinyl Sulfones with Iodine Azide : Synthesis and Thermal Reactions of β-Azidovinyl Sulfones

抄録

p-Toluenesulfonylethene reacted with iodine azide (IN₃) to give 2-azido-1-iodo-1-p-toluenesulfonylethane which was treated with 1, 4-diazabicyclo [2. 2. 2] octane (Dabco) to afford trans-2-azido-1-p-toluenesulfonylethene (3a). Similarly benzenesulfonylethene was converted to trans-2-azido-1-benzenesulfonylethene (3b). cis-and trans-2-Benzenesulfonyl-styrenes also reacted with IN₃ to give threo-(10) and erythro-2-azido-1-iodo-2-phenyl-1-benzenesulfonylethanes (6), respectively. Treatment of 10 with Dabco gave α-azido-β-benzenesulfonylstyrene (11), whereas 6 yielded β-iodo-β-benzenesulfonylstyrene (7). Heating 3 in ethanol at 50°produced dimeric compounds 13. Refluxing 11 in methanol or irradiation of 11 in a Pyrex tube gave 3-benzenesulfonyl-2-phenyl-1-azirine (14).