Unusual Nazarov cyclization in near-critical water

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

doi:10.1021/op050075t

Unusual Nazarov cyclization in near-critical water

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

VTT Technical Research Centre of Finland

University of Helsinki

Research output: Contribution to journal › Article › Scientific › peer-review

8 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 language	English
Pages (from-to)	629-633
Journal	Organic Process Research and Development
Volume	9
Issue number	5
DOIs	https://doi.org/10.1021/op050075t
Publication status	Published - 2005
MoE publication type	A1 Journal article-refereed

Keywords

Nazarov reaction
cyclopentenones
cyclization
ketones

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10.1021/op050075t

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title = "Unusual Nazarov cyclization in near-critical water",

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. ",

keywords = "Nazarov reaction, cyclopentenones, cyclization, ketones",

author = "Tuomo Leikoski and Juha Kaunisto and Martti Alkio and Olli Aaltonen and Jari Yli-Kauhaluoma",

year = "2005",

doi = "10.1021/op050075t",

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T1 - Unusual Nazarov cyclization in near-critical water

AU - Leikoski, Tuomo

AU - Kaunisto, Juha

AU - Alkio, Martti

AU - Aaltonen, Olli

AU - Yli-Kauhaluoma, Jari

PY - 2005

Y1 - 2005

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

M3 - Article

SN - 1083-6160

VL - 9

SP - 629

EP - 633

JO - Organic Process Research and Development

JF - Organic Process Research and Development

IS - 5

ER -

Unusual Nazarov cyclization in near-critical water

Abstract

Keywords

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