Unusual Nazarov cyclization in near-critical water

Tuomo Leikoski, Kaunisto Juha, Martti Alkio, Olli Aaltonen, Jari Yli-Kauhaluoma

Research output: Contribution to journalArticleScientificpeer-review

7 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)629 - 633
Number of pages5
JournalOrganic Process Research and Development
Volume9
Issue number5
DOIs
Publication statusPublished - 2005
MoE publication typeA1 Journal article-refereed

Fingerprint

Cyclization
carbon dioxide
carbonic acid
Carbon Dioxide
acids
Water
Carbonic Acid
water
acetone
minerals
Organic solvents
optimization
Minerals
protons
Protons
products
Acids
cyclopentenone
diphenyl

Keywords

  • Nazarov reaction
  • cyclopentenones
  • cyclization
  • ketones

Cite this

Leikoski, T., Juha, K., Alkio, M., Aaltonen, O., & Yli-Kauhaluoma, J. (2005). Unusual Nazarov cyclization in near-critical water. Organic Process Research and Development, 9(5), 629 - 633. https://doi.org/10.1021/op050075t
Leikoski, Tuomo ; Juha, Kaunisto ; Alkio, Martti ; Aaltonen, Olli ; Yli-Kauhaluoma, Jari. / Unusual Nazarov cyclization in near-critical water. In: Organic Process Research and Development. 2005 ; Vol. 9, No. 5. pp. 629 - 633.
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Leikoski, T, Juha, K, Alkio, M, Aaltonen, O & Yli-Kauhaluoma, J 2005, 'Unusual Nazarov cyclization in near-critical water', Organic Process Research and Development, vol. 9, no. 5, pp. 629 - 633. https://doi.org/10.1021/op050075t

Unusual Nazarov cyclization in near-critical water. / Leikoski, Tuomo; Juha, Kaunisto; Alkio, Martti; Aaltonen, Olli; Yli-Kauhaluoma, Jari.

In: Organic Process Research and Development, Vol. 9, No. 5, 2005, p. 629 - 633.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Unusual Nazarov cyclization in near-critical water

AU - Leikoski, Tuomo

AU - Juha, Kaunisto

AU - Alkio, Martti

AU - Aaltonen, Olli

AU - Yli-Kauhaluoma, Jari

PY - 2005

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N2 - 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.

AB - 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.

KW - Nazarov reaction

KW - cyclopentenones

KW - cyclization

KW - ketones

U2 - 10.1021/op050075t

DO - 10.1021/op050075t

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JO - Organic Process Research and Development

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Leikoski T, Juha K, Alkio M, Aaltonen O, Yli-Kauhaluoma J. Unusual Nazarov cyclization in near-critical water. Organic Process Research and Development. 2005;9(5):629 - 633. https://doi.org/10.1021/op050075t