Preparation of Some Novel Butyl, Butenyl, Butadienyl and Bytynyl Sulfone Electrophiles for Use in Enolate Trapping Studies

Article abstract of DOI:10.1071/CH9950651

The preparation of some novel four-carbon electrophiles and electrophile intermediates is described.Thus, the chlorobutenyl sulfone (5), the iodobutynyl sulfone (6) and the hitherto unreported chlorobutynyl sulfone (4) were prepared.The novel intermediates, containing a chelating imidazolyl functionality, the N-methylimidazolyl sulfides (13)-(15) were also prepared.However, they polymerized rapidly, thus preventing further synthetic manipulations.The preparation of the α-(trimethylsilyl)butadienyl sulfones (17) and (18) is described and the mode of formation of the intermediate α-trimethylsilyl sulfides (21) and (22) from the trimethylsilylbutenyl sulfide (27) is discussed.