Dicationic ring-opening reactions of trans-2-phenylcyclopropylamine·HCl: electrophilic cleavage of the distal (C2-C3) bond of cyclopropanes.
Electrophilic ring opening of trans-2-phenylcyclopropylamine·HCl occurs at the distal (C2-C3) bond. This is consistent with weakening of the distal bond by the σ-withdrawing ammonium group and charge-charge repulsive effects in the transition state.
Department of Chemistry and Molecular Biology, University of Gothenburg, SE-412 96 Gothenburg, Sweden.
Sten O
SO
Nilsson Lill
Rajasekhar Reddy
RR
Naredla
Matthew E
ME
Zielinski
Larecia
L
Knoecer
Douglas A
DA
Klumpp
D000588:Amines / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure
D000588:Amines; D002412:Cations; D003521:Cyclopropanes