Literature DB >> 23209534

The chemistry of bisallenes.

Henning Hopf1, Georgios Markopoulos.   

Abstract

This review describes the preparation, structural properties and the use of bisallenes in organic synthesis for the first time. All classes of compounds containing at least two allene moieties are considered, starting from simple conjugated bisallenes and ending with allenes in which the two cumulenic units are connected by complex polycyclic ring systems, heteroatoms and/or heteroatom-containing tethers. Preparatively the bisallenes are especially useful in isomerization and cycloaddition reactions of all kinds leading to the respective target molecules with high atom economy and often in high yield. Bisallenes are hence substrates for generating molecular complexity in a small number of steps (high step economy).

Entities:  

Keywords:  alicyclic; bisallenes; cyclic; cycloadditions; cycloisomerization; isomerization; molecular complexity; step economy

Year:  2012        PMID: 23209534      PMCID: PMC3511034          DOI: 10.3762/bjoc.8.225

Source DB:  PubMed          Journal:  Beilstein J Org Chem        ISSN: 1860-5397            Impact factor:   2.883


  37 in total

1.  Synthesis of the First

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-12-16       Impact factor: 15.336

2.  Triplet Di(9-anthryl)carbene Undergoes Trimerization This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture of Japan. We thank Prof. Dr. K. Tsujimoto (Japan Advanced Institute of Science and Technology, Hokuriku) for the FAB-MS measurement.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-10-02       Impact factor: 15.336

3.  Highly efficient catalytic synthesis of substituted allenes using indium.

Authors:  Kooyeon Lee; Dong Seomoon; Phil Ho Lee
Journal:  Angew Chem Int Ed Engl       Date:  2002-10-18       Impact factor: 15.336

4.  STUDIES ON ACETYLENIC COMPOUNDS. 38. THE NOVEL CYCLIZATION REACTION OF DIACETYLENIC COMPOUNDS TO NAPHTHALENE DERIVATIVES INVOLVING PROTOTROPIC REARRANGEMENT.

Authors:  I IWAI; J IDE
Journal:  Chem Pharm Bull (Tokyo)       Date:  1964-09       Impact factor: 1.645

5.  What can a metal catalyst do with allenes? One-step formation of steroid scaffolds from readily available starting materials.

Authors:  Shengming Ma; Ping Lu; Lianghua Lu; Hairong Hou; Jiemin Wei; Qiwen He; Zhenhua Gu; Xuefeng Jiang; Xing Jin
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-19       Impact factor: 15.336

6.  Olefin Cycloadditions of the Electrophilic Phosphinidene Complex

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-09       Impact factor: 15.336

7.  Dynamic NMR study of the rotation around "biphenyl-type" bonds in polycyclic sulfoxides.

Authors:  Samuel Braverman; Yossi Zafrani; Hugo E Gottlieb
Journal:  J Org Chem       Date:  2002-05-17       Impact factor: 4.354

8.  Chloroprene as a source of fine chemicals: palladium-catalyzed synthesis of terminal allenes.

Authors:  M Ogasawara; H Ikeda; T Nagano; T Hayashi
Journal:  Org Lett       Date:  2001-08-09       Impact factor: 6.005

9.  Vinylphosphonium Salts and Allenes from Carbonyl Compounds Using Titanium-Substituted Ylides.

Authors:  Kelly A. Reynolds; Pablo G. Dopico; Marcus S. Brody; M. G. Finn
Journal:  J Org Chem       Date:  1997-04-18       Impact factor: 4.354

10.  The synthesis of a dicyclopenta[a,e]pentalene via a molybdenum hexacarbonyl-mediated tandem allenic Pauson-Khand reaction.

Authors:  Hui Cao; Judith Flippen-Anderson; James M Cook
Journal:  J Am Chem Soc       Date:  2003-03-19       Impact factor: 15.419

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  3 in total

1.  Palladium-Catalyzed Oxidative Domino Carbocyclization-Arylation of Bisallenes.

Authors:  Chandra M R Volla; Jan-E Bäckvall
Journal:  ACS Catal       Date:  2016-08-23       Impact factor: 13.084

2.  Solving the puzzling competition of the thermal C(2)-C(6) vs Myers-Saito cyclization of enyne-carbodiimides.

Authors:  Anup Rana; Mehmet Emin Cinar; Debabrata Samanta; Michael Schmittel
Journal:  Beilstein J Org Chem       Date:  2016-01-11       Impact factor: 2.883

3.  Polar reactions of acyclic conjugated bisallenes.

Authors:  Reiner Stamm; Henning Hopf
Journal:  Beilstein J Org Chem       Date:  2013-01-08       Impact factor: 2.883

  3 in total

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