ORGN 299 |
Divinylcyclopropanes and derived cycloheptadienes from the reactions of deprotonated allyl phenyl sufides with 1,3-butadienes
| Theodore Cohen, Xiaojun Liu, Thanapong Kreethadumrongdat, and Yi Xiong Lei. Chemistry Department, University of Pittsburgh, Pittsburgh, PA 15260 |
| During the past 25 years, a number of publications from this laboratory have described synthetic methods based on the formation of cyclopropanes by the intramolecular nucleophilic displacement of a thiophenoxide ion by a lithium-bearing carbon atom. In several of the cases, the reactive species were generated by the carbometallation of an alkene by a sulfur-stabilized organolithium. We now reveal a method for preparing divinylcyclopropanes by the attack of deprotonated allyl phenyl sulfides on various conjugated dienes. Several of the divinylcyclopropanes have been pyrolysed to cycloheptadienes bearing versatile allylic or vinylic phenylthio groups. 
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