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,...
Published in: | Organic Process Research & Development |
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Main Authors: | , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
2005
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Subjects: | |
Online Access: | https://cris.vtt.fi/en/publications/224f4659-766f-4d3b-852a-16f8932c693f https://doi.org/10.1021/op050075t |
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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