33229-02-6Relevant academic research and scientific papers
The Grob/Eschenmoser fragmentation of cycloalkanones bearing β-electron withdrawing groups: A general strategy to acyclic synthetic intermediates
Hierold, Judith,Hsia, Tina,Lupton, David W.
experimental part, p. 783 - 792 (2011/03/21)
Introduction of a β-electron withdrawing group to cycloalkanones allows facile C-C bond fragmentation. The reaction has been demonstrated with a large range of ring sizes, bearing various leaving and electron withdrawing groups, and using a variety of nitrogen and oxygen containing nucleophiles (>30 examples). The application of fragmentation products to the preparation of substituted γ-lactones has been demonstrated. Mechanistic studies are reported which are suggestive of a Grob/Eschenmoser type reaction.
