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Synthesis and Claisen rearrangement of bridged bicyclic enol ethers of relevance to the course of ketene s-cis-diene cycloaddition.

Abstract:
The synthesis is described of a range of 3-alkylidene-2-oxabicyclo[2.2.1]hept-5-ene and 3-alkylidene-2-oxabicyclo[2.2.2]oct-5-ene derivatives; Claisen rearrangement of these substrates either thermally or in the presence of an added Lewis acid results in the formation of bicyclic cyclobutanones with generally good conversions. These reactions may be performed in hydroxylic solvents, supporting a largely non-dissociative pathway for the rearrangement.
Publication status:
Published

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Publisher copy:
10.1039/b611311g

Authors


More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Fowler, TG More by this author
Journal:
Organic and biomolecular chemistry
Volume:
4
Issue:
23
Pages:
4307-4318
Publication date:
2006-12-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:dca657b8-57a1-4418-b5f1-a1b9d52900f9
Source identifiers:
55223
Local pid:
pubs:55223
Language:
English

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