Jump to main content
Jump to site search

Issue 6, 2010
Previous Article Next Article

Cyclopropenium-activated Beckmann rearrangement. Catalysis versus self-propagation in reported organocatalytic Beckmann rearrangements

Author affiliations

Abstract

The concept of cyclopropenium activation has been extended to include dehydrative rearrangements in the context of the Beckmann rearrangement. Geminal dichlorocyclopropenes are shown to rapidly and efficiently convert oximes to amides at room temperature, with reactivity that far surpasses other organic-based promoters. Twelve total examples are provided, including a complex steroidal substrate on preparative scale. Evidence is provided that suggests previously reported organocatalytic Beckmann rearrangements may in fact be self-propagating rather than catalytic.

Graphical abstract: Cyclopropenium-activated Beckmann rearrangement. Catalysis versus self-propagation in reported organocatalytic Beckmann rearrangements

Back to tab navigation

Supplementary files

Publication details

The article was received on 09 Aug 2010, accepted on 14 Sep 2010 and first published on 12 Oct 2010


Article type: Edge Article
DOI: 10.1039/C0SC00421A
Citation: Chem. Sci., 2010,1, 705-708
  •   Request permissions

    Cyclopropenium-activated Beckmann rearrangement. Catalysis versus self-propagation in reported organocatalytic Beckmann rearrangements

    C. M. Vanos and T. H. Lambert, Chem. Sci., 2010, 1, 705
    DOI: 10.1039/C0SC00421A

Search articles by author

Spotlight

Advertisements