Literature DB >> 19513183

An unusual norcaradiene/tropylium rearrangement from a persistent amino-phosphonio-carbene.

Joan Vignolle1, Bruno Donnadieu, Didier Bourissou, Guy Bertrand.   

Abstract

An amino-phosphonio-carbene featuring a bromobiphenyl backbone was prepared and spectroscopically characterized at low temperature. This carbene was found to readily rearrange upon warm up, affording an original tricyclic phospholium derivative, presumably via a norcaradiene/tropylium isomerization.

Entities:  

Year:  2007        PMID: 19513183      PMCID: PMC2692173          DOI: 10.1016/j.tetlet.2006.11.099

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  18 in total

1.  Stable Carbenes.

Authors:  Didier Bourissou; Olivier Guerret; François P. Gabbaï; Guy Bertrand
Journal:  Chem Rev       Date:  2000-01-12       Impact factor: 60.622

2.  Modified BINAP: the how and the why.

Authors:  Mikaël Berthod; Gérard Mignani; Gary Woodward; Marc Lemaire
Journal:  Chem Rev       Date:  2005-05       Impact factor: 60.622

3.  Stable cyclic (alkyl)(amino)carbenes as rigid or flexible, bulky, electron-rich ligands for transition-metal catalysts: a quaternary carbon atom makes the difference.

Authors:  Vincent Lavallo; Yves Canac; Carsten Präsang; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-05       Impact factor: 15.336

Review 4.  Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis.

Authors:  Vincent César; Stéphane Bellemin-Laponnaz; Lutz H Gade
Journal:  Chem Soc Rev       Date:  2004-11-03       Impact factor: 54.564

5.  (Amino)(aryl)carbenes: stable singlet carbenes featuring a spectator substituent.

Authors:  S Solé; H Gornitzka; W W Schoeller; D Bourissou; G Bertrand
Journal:  Science       Date:  2001-06-08       Impact factor: 47.728

6.  Stable versions of transient push-pull carbenes: extending lifetimes from nanoseconds to weeks

Authors: 
Journal:  Science       Date:  2000-05-05       Impact factor: 47.728

7.  Stable non-push-pull phosphanylcarbenes: NMR spectroscopic characterization of a methylcarbene.

Authors:  Emmanuelle Despagnet; Heinz Gornitzka; Alexander B Rozhenko; Wolfgang W Schoeller; Didier Bourissou; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2002-08-02       Impact factor: 15.336

8.  EPR and DFT studies of the one-electron reduction product of phospholium cations.

Authors:  Prashant Adkine; Thibault Cantat; Eliane Deschamps; Louis Ricard; Nicolas Mézailles; Pascal Le Floch; Michel Geoffroy
Journal:  Phys Chem Chem Phys       Date:  2005-12-19       Impact factor: 3.676

9.  Synthesis of carbenes through substitution reactions at a carbene center.

Authors:  Nathalie Merceron-Saffon; Antoine Baceiredo; Heinz Gornitzka; Guy Bertrand
Journal:  Science       Date:  2003-08-29       Impact factor: 47.728

10.  N-heterocyclic carbenes: a new concept in organometallic catalysis.

Authors:  Wolfgang A Herrmann
Journal:  Angew Chem Int Ed Engl       Date:  2002-04-15       Impact factor: 15.336

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