Cycloaddition of Bu(n)3P·CS2: Direct one-pot conversion of strained double bonds to 2-alkylidene-1,3-dithiolanes

Article abstract of DOI:10.1016/S0040-4020(96)01128-3

Reaction of the adduct between tri-n-butylphosphine and carbon disulfide 1 with norbornene gives the novel zwitterionic structure 9. In solution this dissociates to the ylide 8 which undergoes Wittig reaction with aldehydes. Using the same method, the overall conversion of the strained double bond in a variety of bicyclo[2.2.1]alkenes into 2-benzylidene-1,3-dithioles 15-24 has been achieved and the reaction is also applicable to norbonnadiene, affording bis-dithiolanes 29-31.