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- Title
Regiodivergent Chlorine-Atom-Transfer Ring-Opening Reactions of Trichloromethylcyclopropanes.
- Authors
Doi, Nobuyoshi; Takeda, Norihiko; Miyata, Okiko; Ueda, Masafumi
- Abstract
A regiodivergent chlorine-atom-transfer reaction involving the ring-opening of trichloromethylcyclopropanes was developed. Treatment of a trichloromethylcyclopropane with ZnMe2 provided the β-chloro-α-dichlorovinyl ester with high stereoselectivity through a chloride-anion-mediated atomtransfer ring-opening reaction. In contrast, the use of CuCl afforded the α-chloro-β-dichlorovinyl ester by a chlorine-radicalmediated atom-transfer ring-opening reaction.
- Subjects
CYCLOPROPANE; ATOM transfer reactions; TRICHLOROMETHYL group; RING-opening reactions; CHLORINE compounds; STEREOSELECTIVE reactions
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 25, p3652
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201700567