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Dicationic ring-opening reactions of trans-2-phenylcyclopropylamine·HCl: electrophilic cleavage of the distal (C2-C3) bond of cyclopropanes.

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 ?-withdrawing ammonium group and charge-charge repulsive effects in the transition state.

SUBMITTER: Nilsson Lill SO

PROVIDER: S-EPMC5333643 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Dicationic ring-opening reactions of trans-2-phenylcyclopropylamine·HCl: electrophilic cleavage of the distal (C2-C3) bond of cyclopropanes.

Nilsson Lill Sten O SO Naredla Rajasekhar Reddy RR Zielinski Matthew E ME Knoecer Larecia L Klumpp Douglas A DA

The Journal of organic chemistry 20130826 17

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. ...[more]

PMID: 23941589

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