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

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 i...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2015-03, Vol.51 (20), p.4204-4207
Main Authors: Ueda, Masafumi, Doi, Nobuyoshi, Miyagawa, Hitoki, Sugita, Shoichi, Takeda, Norihiko, Shinada, Tetsuro, Miyata, Okiko
Format: Article
Language:English
Subjects:
Boranes - chemistry
Carbon Tetrachloride - analogs & derivatives
Carbon Tetrachloride - chemistry
Cascade chemical reactions
Chloroform
Chloroform - chemistry
Cyclopropanes - chemistry
Esters
Formations
Initiators
Migration
Organic compounds
Organometallic Compounds - chemistry
Radicals
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc09649e