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Paper | Special issue | Vol 40, No. 1, 1995, pp.191-204
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S8
1,3-Dipolar Cycloaddition Chemistry of 2,3-Bis(phenylsulfonyl)-1,3-diene with Diazoalkanes

Albert Padwa, Michael Meske, and Augusto Rodoriguez

*Department of Chemistry, Emory University, 1515 Pierce Drive Atlanta, Georgia 30322, U.S.A.


2,3-Bis(phenylsulfonyl)-1,3-butadiene was found to react smoothly with diazomethane and diazopropane to give a mixture of 1:1- and 2:1-cycloadducts. Heating the 1:1-cycloadduct at 110°C resulted in loss of nitrogen and formation of mainly phenylsulfonyl-substituted 1,3-dienes. Cycloaddition of 2-phenylsulfinyl-3-phenylsulfonyl-1,3-butadiene with the same diazoalkanes gave only 1:1-cycloadducts which readily extruded nitrogen producing related 1,3-dienes. The regiochemistry of the dipolar cycloaddition is compatible with FMO considerations.