Unusual Nazarov cyclization in near-critical water

The Nazarov reaction of trans , trans -dibenzylidene acetone in near-critical water with or without additional carbon dioxide produces 2,3-diphenyl-2-cyclopentenone instead of the conventional Nazarov product, 3,4-disubstituted 2-cyclopentenone. The use of organic solvents and strong mineral acids,...

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Bibliographic Details
Published in:Organic Process Research & Development
Main Authors: Leikoski, Tuomo, Kaunisto, Juha, Alkio, Martti, Aaltonen, Olli, Yli-Kauhaluoma, Jari
Format: Article in Journal/Newspaper
Language:English
Published: 2005
Subjects:
Nazarov reaction
cyclopentenones
cyclization
ketones
Carbonic acid
Online Access:https://cris.vtt.fi/en/publications/224f4659-766f-4d3b-852a-16f8932c693f
https://doi.org/10.1021/op050075t
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Summary:The Nazarov reaction of trans , trans -dibenzylidene acetone in near-critical water with or without additional carbon dioxide produces 2,3-diphenyl-2-cyclopentenone instead of the conventional Nazarov product, 3,4-disubstituted 2-cyclopentenone. The use of organic solvents and strong mineral acids, generally required for this reaction, is avoided by using water and carbonic acid as a proton source. After an optimization procedure, 38% yield of 2,3-diphenyl-2-cyclopentenone was obtained. The presence of carbon dioxide had a clear positive effect on yield.

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