Reaction of cyclopropenes with a trichloromethyl radical: unprecedented ring-opening reaction of cyclopropanes with migration.

Masafumi Ueda, Nobuyoshi Doi, Hitoki Miyagawa, Shoichi Sugita, Norihiko Takeda, Tetsuro Shinada, Okiko Miyata

Chemical communications (Cambridge, England) 2015 Mar 11

filter terms:

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.

Citation

Masafumi Ueda, Nobuyoshi Doi, Hitoki Miyagawa, Shoichi Sugita, Norihiko Takeda, Tetsuro Shinada, Okiko Miyata. Reaction of cyclopropenes with a trichloromethyl radical: unprecedented ring-opening reaction of cyclopropanes with migration. Chemical communications (Cambridge, England). 2015 Mar 11;51(20):4204-7