title: 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.
abstract: 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.
authors: Department of Chemistry and Bioengineering, Faculty of Engineering, Iwate University, Morioka, Iwate 020-8551, Japan. shimada@iwate-u.ac.jp
authors: Kazuaki
authors: K
authors: Shimada
authors: Jun
authors: J
authors: Sasaki
authors: Anna
authors: A
authors: Kishi
authors: Shigenobu
authors: S
authors: Aoyagi
authors: Yuji
authors: Y
authors: Takikawa
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D001892:Camphanes / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000475:Alkenes; D001892:Camphanes; C030011:carbene; D008697:Methane