Synthesis of Sterically-Crowded Olefins,gem -Dihaloalkenes,Butatrienes,and Thioketenes through the Reaction of Substituted Bornane-2-thiones or Bornane-2-selones with Conventional Carbenes or Metal Carbenoids
Free accessResearch articleFirst published online July, 2013
Synthesis of Sterically-Crowded Olefins,gem -Dihaloalkenes,Butatrienes,and Thioketenes through the Reaction of Substituted Bornane-2-thiones or Bornane-2-selones with Conventional Carbenes or Metal Carbenoids
Reaction of highly-substituted bornane-2-selones with a diazoalkane in the presence of either Rh2(OAc)4 or CuCl formed sterically-crowded exo-methylenic products, and similar treatment of the thiones or selones with dihalocarbenes or a propadienylidene carbene also formed dihaloalkenes, butatrienes, and thioketenes. All these reactions were assumed to proceed through a pathway involving the in situ formation and subsequent ring closure of chalcogenocarbonyl ylides.
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