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.
Reaction of Cyclopropenes with a Trichloromethyl Radical: Unprecedented Ring--Opening Reaction of Cyclopropanes with Migration. -The direct addition reaction of chloroform to cyclopropenes in presence of triethylborane as initiator gives trichloromethylated cyclopropanes in good yields. By using dimethylzinc as radical initiator linear products are obtained by a domino sequence involving the addition of trichloromethyl radical followed by rearrangement and ring-opening reaction. -(UEDA, M.; DOI, N.; MIYAGAWA, H.; SUGITA, S.; TAKEDA, N.; SHINADA, T.; MIYATA*, O.; Chem. Commun. (Cambridge) 51 (2015) 20, 4204-4207, http://dx.doi.org/10.1039/C4CC09649E ; Kobe Pharm. Univ., Higashinada, Kobe 658, Japan; Eng.) -B. Bergmann 28-082
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