Furan Forming Reactions of cis-2-Alken-4-yn-1-ones

The cis-2-alken-4-yn-1-one, 1-phenyl-cis-2-penten-4-yn-1-one (cis -1), readily dimerizes on treatment with weak acid to give the 1,2-difurylethylenes, trans- and cis-1,2 di(2-(5-phenylfuryl))ethene (trans-1 and cis-2), in 62% and 23% yields, respectively. Trimerization of cis-1 to trans,trans-1,2,3-...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-04, Vol.70 (7), p.2576-2581
Main Authors: Casey, Charles P, Strotman, Neil A
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:The cis-2-alken-4-yn-1-one, 1-phenyl-cis-2-penten-4-yn-1-one (cis -1), readily dimerizes on treatment with weak acid to give the 1,2-difurylethylenes, trans- and cis-1,2 di(2-(5-phenylfuryl))ethene (trans-1 and cis-2), in 62% and 23% yields, respectively. Trimerization of cis-1 to trans,trans-1,2,3-tri(2-(5-phenylfuryl)cyclopropane (4) occurred as a byproduct of treatment with weak acid. These reactions demonstrate the 2-furylcarbenoid reactivity of cis-2-alken-4-yn-1-ones.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo047762n