Dicationic ring-opening reactions of trans -2- phenylcyclopropylamine·HCl: Electrophilic cleavage of the distal (C 2-C3) bond of cyclopropanes

Sten O. Nilsson Lill, Rajasekhar Reddy Naredla, Matthew E. Zielinski, Larecia Knoecer, Douglas A. Klumpp

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)8922-8926
Number of pages5
JournalJournal of Organic Chemistry
Volume78
Issue number17
DOIs
StatePublished - Sep 6 2013

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