Literature DB >> 19128149

Mechanistic aspects of alkyne migration in alkylidene carbenoid rearrangements.

Paul Bichler1, Wesley A Chalifoux, Sara Eisler, Annabelle L K Shi Shun, Erin T Chernick, Rik R Tykwinski.   

Abstract

The mechanism of the Fritsch-Buttenberg-Wiechell rearrangement of (13)C labeled precursors has been examined to determine the propensity of the alkynyl (R-CC-) group to migrate in an alkylidene carbenoid species. Reaction of dibromoolefins with n-BuLi and ketones with Me(3)SiC(Li)N(2) both demonstrate that the alkynyl moiety readily undergoes 1,2-migration from carbenoid intermediates.

Entities:  

Year:  2009        PMID: 19128149     DOI: 10.1021/ol8023665

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  1 in total

1.  Nickel-Catalyzed Anionic Cross-Coupling Reaction of Lithium Sulfonimidoyl Alkylidene Carbenoids With Organolithiums.

Authors:  Irene Erdelmeier; Joonghee Won; Steve Park; Jürgen Decker; Gerd Bülow; Mu-Hyun Baik; Hans-Joachim Gais
Journal:  Chemistry       Date:  2020-02-20       Impact factor: 5.236

  1 in total

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