Literature DB >> 29200937

Diverse modes of reactivity of 6-(chloromethyl)-6-methylfulvene.

Ihsan Erden1, Scott Gronert2, Gabriel Cabrera1, Necdet Coskun3, Marco Tapken1.   

Abstract

The title compound exhibits a number of reactivities toward nucleophiles/bases owing to the presence of several electrophilic and potentially nucleophilic sites in the molecule. We explored the reactions of 6-(chloromethyl)-6-methylfulvene with oxygen- and nitrogen nucleophiles and bases as well as a carbon-based nucleophile (an enamine) and realized all possible reactivity modes predicted on the basis of electrophilic and nucleophilic positions in this compound.

Entities:  

Keywords:  1,2-Dihydropentalene; Dipolar cycloaddition; E1cB; Fulvenes; Nucleophilic addition

Year:  2017        PMID： 29200937      PMCID： PMC5708559          DOI： 10.1002/ejoc.201700442

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  9 in total

1.  From 6-t-butylfulvene to highly functionalized five-membered rings.

Authors:  J Baumgartner; H Weber
Journal:  Chirality       Date:  2001       Impact factor: 2.437

2.  Unusual hydroxyl effect on fulvene endoperoxide decompositions.

Authors:  Ihsan Erden; John Basada; Daniela Poli; Gabriel Cabrera; Fupei Xu; Scott Gronert
Journal:  Tetrahedron Lett       Date:  2016-05-18       Impact factor: 2.415

3.  An efficient catalytic method for fulvene synthesis.

Authors:  Necdet Coşkun; Ihsan Erden
Journal:  Tetrahedron       Date:  2011-11-11       Impact factor: 2.457

4.  1,2-Dihydropentalenes from fulvenes by [6 + 2] cycloadditions with 1-isopropenylpyrrolidine.

Authors:  Necdet Coşkun; Jingxiang Ma; Saeed Azimi; Christian Gärtner; Ihsan Erden
Journal:  Org Lett       Date:  2011-10-26       Impact factor: 6.005

5.  Substituent effects on the electron affinities and ionization energies of tria-, penta-, and heptafulvenes: a computational investigation.

Authors:  Christian Dahlstrand; Kaoru Yamazaki; Kristine Kilså; Henrik Ottosson
Journal:  J Org Chem       Date:  2010-11-10       Impact factor: 4.354

6.  Azadiene Diels-Alder cycloaddition of fulvenes: a facile approach to the [1]pyrindine system.

Authors:  Bor-Cherng Hong; Jian-Lin Wu; Arun Kumar Gupta; Mahanandeesha Siddappa Hallur; Ju-Hsiou Liao
Journal:  Org Lett       Date:  2004-09-30       Impact factor: 6.005

7.  Novel [6 + 2] cycloaddition of fulvenes with alkenes: a facile synthesis of the anislactone and hirsutane framework.

Authors:  Bor-Cherng Hong; Yeong-Jou Shr; Jian-Lin Wu; Arun Kumar Gupta; Kuan-Jiuh Lin
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

8.  An exceptionally simple and efficient synthesis of 6-methyl-6-vinylfulvene, and its oxidative transformations.

Authors:  Ihsan Erden; Christian Gärtner
Journal:  Tetrahedron Lett       Date:  2009-05-20       Impact factor: 2.415

9.  Effect of allylic groups on S(N)2 reactivity.

Authors:  Ihsan Erden; Scott Gronert; James R Keeffe; Jingxiang Ma; Nuket Ocal; Christian Gärtner; Leah L Soukup
Journal:  J Org Chem       Date:  2014-07-07       Impact factor: 4.354
  9 in total

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