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

doi:10.1039/c4cc09649e

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

Chem Commun (Camb). 2015 Mar 11;51(20):4204-7. doi: 10.1039/c4cc09649e.

Authors

Masafumi Ueda¹, Nobuyoshi Doi, Hitoki Miyagawa, Shoichi Sugita, Norihiko Takeda, Tetsuro Shinada, Okiko Miyata

Affiliation

¹ Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan. miyata@kobepharma-u.ac.jp.

PMID: 25578613
DOI: 10.1039/c4cc09649e

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Boranes / chemistry
Carbon Tetrachloride / analogs & derivatives*
Carbon Tetrachloride / chemistry
Chloroform / chemistry*
Cyclopropanes / chemistry*
Organometallic Compounds / chemistry

Substances

Boranes
Cyclopropanes
Organometallic Compounds
trichloromethyl free radical
cyclopropene
Chloroform
dimethylzinc
Carbon Tetrachloride
triethylborane