Literature DB >> 23842904

Accelerating influence of the gem-difluoromethylene group in a ring-closing olefin metathesis reaction. A Thorpe-Ingold effect?

César A Urbina-Blanco1, Maciej Skibiński, David O'Hagan, Steven P Nolan.   

Abstract

The gem-difluoromethylene (CF2) group significantly accelerates ring-closing metathesis of 1,8-nonadienes relative to the methylene (CH2) group demonstrating similar rate accelerations to that observed for the classic Thorpe-Ingold substituents, diester malonates and ketals.

Entities:  

Year:  2013        PMID： 23842904     DOI： 10.1039/c3cc44312d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  5 in total

1.  Combining a Clostridial enzyme exhibiting unusual active site plasticity with a remarkably facile sigmatropic rearrangement: rapid, stereocontrolled entry into densely functionalized fluorinated phosphonates for chemical biology.

Authors:  Kaushik Panigrahi; Gregory A Applegate; Guillaume Malik; David B Berkowitz
Journal:  J Am Chem Soc       Date:  2015-03-05       Impact factor: 15.419

2.  The difluoromethylene (CF2) group in aliphatic chains: Synthesis and conformational preference of palmitic acids and nonadecane containing CF2 groups.

Authors:  Yi Wang; Ricardo Callejo; Alexandra M Z Slawin; David O'Hagan
Journal:  Beilstein J Org Chem       Date:  2014-01-06       Impact factor: 2.883

3.  Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes.

Authors:  Otome E Okoromoba; Junbin Han; Gerald B Hammond; Bo Xu
Journal:  J Am Chem Soc       Date:  2014-10-02       Impact factor: 15.419

4.  Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring.

Authors:  Mathew J Jones; Ricardo Callejo; Alexandra M Z Slawin; Michael Bühl; David O'Hagan
Journal:  Beilstein J Org Chem       Date:  2016-12-22       Impact factor: 2.883

5.  Coupling of α,α-difluoro-substituted organozinc reagents with 1-bromoalkynes.

Authors:  Artem A Zemtsov; Alexander D Volodin; Vitalij V Levin; Marina I Struchkova; Alexander D Dilman
Journal:  Beilstein J Org Chem       Date:  2015-11-10       Impact factor: 2.883
  5 in total

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