title: Reaction of cyclopropenes with a trichloromethyl radical: unprecedented ring-opening reaction of cyclopropanes with migration.
abstract: The direct addition reaction of chloroform to cyclopropenes under triethylborane-mediated radical reaction conditions to provide trichloromethylcyclopropanes has been developed. In contrast, using dimethylzinc as a radical initiator led to the formation of unconjugated esters via a domino sequence involving the addition of the trichloromethyl radical, rearrangement and ring-opening reactions.
authors.affiliation: Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan. miyata@kobepharma-u.ac.jp.
authors.forename: Masafumi
authors.initials: M
authors.lastname: Ueda
authors.forename: Nobuyoshi
authors.initials: N
authors.lastname: Doi
authors.forename: Hitoki
authors.initials: H
authors.lastname: Miyagawa
authors.forename: Shoichi
authors.initials: S
authors.lastname: Sugita
authors.forename: Norihiko
authors.initials: N
authors.lastname: Takeda
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Shinada
authors.forename: Okiko
authors.initials: O
authors.lastname: Miyata
mesh_terms: D001880:Boranes / Q000737:chemistry; D002251:Carbon Tetrachloride / Q000031:analogs & derivatives* / Q000737:chemistry; D002725:Chloroform / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry
chemical_list: D001880:Boranes; D003521:Cyclopropanes; D009942:Organometallic Compounds; C025280:trichloromethyl free radical; C021985:cyclopropene; D002725:Chloroform; C511262:dimethylzinc; D002251:Carbon Tetrachloride; C079756:triethylborane