Standard Article

Weiss-Cook Condensation

(Weiss Reaction, Weiss-Cook Reaction)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr662

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Weiss-Cook Condensation. Comprehensive Organic Name Reactions and Reagents. 662:2968–2974.

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

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Abstract

The condensation between an α-dicarbonyl molecule and 2 equivalents of 3-oxoglutarate (or dialkyl 1,3-acetonedicarboxylate) in a slightly acidic aqueous media (pH = 5) to form a cis-bicyclo[3.3.0]octane-3,7-dione derivative after acidic hydrolysis and decarboxylation is known as the Weiss reaction. This reaction is also known as the Weiss–Cook condensation because of the contribution by Weiss and his student Cook for the synthesis of multicyclic polyquinane systems. The present study addresses all the features of this reaction and compare it with the Diels-Alder reaction. It has been reported that the Weiss–Cook condensation involves a series of thermodynamic equilibria during the cyclization that favor the cis isomer over its trans isomer. It has also been observed that the Weiss–Cook condensation also takes place under basic conditions. This reaction has been used for the syntheses of a series of fused molecules (e.g., polyquinanes and polyquinenes), which are otherwise prepared by much more complicated procedures.

Keywords:

  • 3-oxoglutarate;
  • cis isomer;
  • dimethyl 2,3-dioxobutanedioate;
  • polyquinanes

Featured Compounds

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  1. 1 - 19
Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3
Molecular Weight:190.3245
Molecular Formula:C14H22
InChIKey:WMCWCDIVHXOHBV-IWMBGFJWSA-N
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Compound 4
Molecular Weight:182.261
Molecular Formula:C14H14
InChIKey:DFFIJDXKOYQNCL-FEPKRQSRSA-N
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Compound 5
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:HKRMLKXSBBQRIM-YNFQOJQRSA-N
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Compound 6
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:WQTCNEZIAZOGRU-QRHSGQBVSA-N
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Compound 7
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:HJEFUJDHUOYCAO-QRHSGQBVSA-N
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Compound 8
Molecular Weight:176.2979
Molecular Formula:C13H20
InChIKey:BMERAHPUZDFYEY-ZSLJRAHMSA-N
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Compound 9
Molecular Weight:168.2344
Molecular Formula:C13H12
InChIKey:SQJMKMUAOUQFAV-ZSLJRAHMSA-N
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Compound 10
Molecular Weight:190.3245
Molecular Formula:C14H22
InChIKey:FYJSMJBCDNJROC-OKILXGFUSA-N
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Compound 11
Molecular Weight:176.2133
Molecular Formula:C14H8
InChIKey:CTEKHOMQVRCHMY-UHFFFAOYSA-N
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Compound 12
Molecular Weight:176.2133
Molecular Formula:C14H8
InChIKey:ZZJMNDSMLMOHEC-UHFFFAOYSA-N
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Compound 13
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 14
Molecular Weight:310.3917
Molecular Formula:C22H18N2
InChIKey:HLWBZOOWIZZFII-UHFFFAOYSA-N
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Compound 15
Molecular Weight:152.1919
Molecular Formula:C12H8
InChIKey:LEVPNPUFJPHRAO-UHFFFAOYSA-N
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Compound 16
Molecular Weight:268.4363
Molecular Formula:C20H28
InChIKey:DZSCEVRMFJFZTM-UHFFFAOYSA-N
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Compound 17
Molecular Weight:190.2399
Molecular Formula:C15H10
InChIKey:ATHDPHZMYVEZIS-UHFFFAOYSA-N
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Compound 18
Molecular Weight:184.2768
Molecular Formula:C14H16
InChIKey:YOINCTKZLQTAEX-KPWCQOOUSA-N
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Compound 19
Molecular Weight:164.2026
Molecular Formula:C13H8
InChIKey:ZAKJSYYBGZODRU-UHFFFAOYSA-N
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  1. 1 - 19