Bicyclo[4.2.0]octanols can be obtained from the reaction of phenyl vinyl sulfoxide and the lithium enolate of cyclohexanone under controlled conditions. Diversion to alkylation or Michael-Michael-ring closure was observed when alternative vinyl electrophiles were used. Novel bicyclic disulfones and hydroxyhexahydronaphthalenes were isolated. The use of a vinyl sulfoxide electrophile is crucial to the formation of bicyclo[4.2.0]octanols from simple ketones.