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

doi:10.1021/jo4016198

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 journal › Article › peer-review

3 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 language	English (US)
Pages (from-to)	8922-8926
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	78
Issue number	17
DOIs	https://doi.org/10.1021/jo4016198
State	Published - Sep 6 2013
Externally published	Yes

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Dicationic ring-opening reactions of trans -2- phenylcyclopropylamine·HCl: Electrophilic cleavage of the distal (C ₂-C₃) bond of cyclopropanes. / Nilsson Lill, Sten O.; Naredla, Rajasekhar Reddy; Zielinski, Matthew E. et al.
In: Journal of Organic Chemistry, Vol. 78, No. 17, 06.09.2013, p. 8922-8926.

Research output: Contribution to journal › Article › peer-review

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title = "Dicationic ring-opening reactions of trans -2- phenylcyclopropylamine·HCl: Electrophilic cleavage of the distal (C 2-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 σ-withdrawing ammonium group and charge-charge repulsive effects in the transition state.",

author = "{Nilsson Lill}, {Sten O.} and Naredla, {Rajasekhar Reddy} and Zielinski, {Matthew E.} and Larecia Knoecer and Klumpp, {Douglas A.}",

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T2 - Electrophilic cleavage of the distal (C 2-C3) bond of cyclopropanes

AU - Nilsson Lill, Sten O.

AU - Naredla, Rajasekhar Reddy

AU - Zielinski, Matthew E.

AU - Knoecer, Larecia

AU - Klumpp, Douglas A.

PY - 2013/9/6

Y1 - 2013/9/6

N2 - 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.

AB - 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.

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

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