Literature DB >> 19737015

Allene synthesis via C-C fragmentation: method and mechanistic insight.

Robert V Kolakowski1, Madhuri Manpadi, Yue Zhang, Thomas J Emge, Lawrence J Williams.   

Abstract

A new method of allene synthesis is described. Suitably functionalized vinyl triflates undergo fragmentation to give allenes in high yield. Computational and experimental data provide a mechanistic framework for allene formation and the complementary formation of alkynes. The method is stereospecific.

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Year:  2009        PMID: 19737015     DOI: 10.1021/ja906189h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  3 in total

1.  Equilibrium between a vinylogous ylide and a phosphonium dienolate zwitterion: vinylogous Wittig olefination versus vinylogous aldol-type reaction.

Authors:  San N Khong; Yang S Tran; Ohyun Kwon
Journal:  Tetrahedron       Date:  2010-06       Impact factor: 2.457

2.  Toward an integrated route to the vernonia allenes and related sesquiterpenoids.

Authors:  Da Xu; Michael A Drahl; Lawrence J Williams
Journal:  Beilstein J Org Chem       Date:  2011-07-05       Impact factor: 2.883

3.  Tipping the balance: theoretical interrogation of divergent extended heterolytic fragmentations.

Authors:  Croix J Laconsay; Ka Yi Tsui; Dean J Tantillo
Journal:  Chem Sci       Date:  2020-01-09       Impact factor: 9.825

  3 in total

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