Literature DB >> 23941589

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

Sten O Nilsson Lill1, Rajasekhar Reddy Naredla, Matthew E Zielinski, Larecia Knoecer, Douglas A Klumpp.   

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.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23941589      PMCID： PMC5333643          DOI： 10.1021/jo4016198

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  16 in total

1.  Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis.

Authors:  Hans-Ulrich Reissig; Reinhold Zimmer
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  Rapid generation of molecular complexity in the Lewis or Brønsted acid-mediated reactions of methylenecyclopropanes.

Authors:  Min Shi; Jian-Mei Lu; Yin Wei; Li-Xiong Shao
Journal:  Acc Chem Res       Date:  2011-12-13       Impact factor: 22.384

3.  Conformation and geometry of cyclopropane rings having π-acceptor substituents: a theoretical and database study.

Authors:  Aurora J Cruz-Cabeza; Frank H Allen
Journal:  Acta Crystallogr B       Date:  2010-12-18

4.  Photoinduced Cleavage of N-N Bonds of Aromatic Hydrazines and Hydrazides by Visible Light.

Authors:  Mingzhao Zhu; Nan Zheng
Journal:  Synthesis (Stuttg)       Date:  2011-06-21       Impact factor: 3.157

5.  Boronate urea activation of nitrocyclopropane carboxylates.

Authors:  Sonia S So; Tyler J Auvil; Victoria J Garza; Anita E Mattson
Journal:  Org Lett       Date:  2011-12-30       Impact factor: 6.005

6.  Chemical and biological properties of some aminomethyl-2-phenylcyclopropane derivatives. Pharmacological comparison with tranylcypromine.

Authors:  U M Teotino; D D Bella; A Gandini; G Benelli
Journal:  J Med Chem       Date:  1967-11       Impact factor: 7.446

7.  Reactions of amino alcohols in superacid: the direct observation of dicationic intermediates and their application in synthesis.

Authors:  D A Klumpp; S L Aguirre; G V Sanchez; S J de Leon
Journal:  Org Lett       Date:  2001-08-23       Impact factor: 6.005

8.  Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloadditions of substituted vinylcyclopropanes.

Authors:  Barry M Trost; Patrick J Morris; Simon J Sprague
Journal:  J Am Chem Soc       Date:  2012-10-10       Impact factor: 15.419

9.  A mild procedure for the Lewis acid-catalyzed ring-opening of activated cyclopropanes with amine nucleophiles.

Authors:  Olga Lifchits; André B Charette
Journal:  Org Lett       Date:  2008-06-04       Impact factor: 6.005

10.  Side-arm-promoted highly enantioselective ring-opening reactions and kinetic resolution of donor-acceptor cyclopropanes with amines.

Authors:  You-Yun Zhou; Li-Jia Wang; Jun Li; Xiu-Li Sun; Yong Tang
Journal:  J Am Chem Soc       Date:  2012-05-24       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.