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词条 Perkin reaction
释义

  1. Reaction mechanism

  2. Applications

  3. See also

  4. References

{{Use dmy dates|date=June 2013}}{{Reactionbox
| verifiedrevid = 342064841
| Type = Condensation reaction
| NamedAfter = William Henry Perkin
| Section2 = {{Reactionbox Identifiers
| RSC_ontology_id_verified = rsccite
| RSC_ontology_id = 0000003
| Reaction = {{Reactionbox Reaction
| Reactant1 = Aromatic aldehyde
| Reactant2 = Aliphatic Acid anhydride
| Reagent1 = Alkali salt of the acid
| Product1 = Cinnamic acid derivatives
}}

The Perkin reaction is an organic reaction developed by English chemist William Henry Perkin that is used to make cinnamic acids. It gives an α,β-unsaturated aromatic acid by the aldol condensation of an aromatic aldehyde and an acid anhydride, in the presence of an alkali salt of the acid.[1][2] The alkali salt acts as a base catalyst, and other bases can be used instead.[3]

Several reviews have been written.[4][5][6]

Reaction mechanism

The above mechanism is not universally accepted, as several other versions exist, including decarboxylation without acetic group transfer.[7]

Applications

  • One notable application for the Perkin reaction is in the laboratory synthesis of the phytoestrogenic stilbene resveratrol (c.f. fo-ti).[8]

See also

  • Erlenmeyer–Plöchl azlactone and amino-acid synthesis
  • Stobbe condensation
  • Pechmann condensation

References

1. ^{{cite journal|author=Perkin, W. H.|journal=Journal of the Chemical Society|year=1868|volume=21|pages= 53–61|doi=10.1039/js8682100053|title= On the artificial production of coumarin and formation of its homologues|url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015077817479;view=1up;seq=65 }}
2. ^{{cite journal|author=Perkin, W. H.|journal=Journal of the Chemical Society|year=1877|volume=32|pages= 660–674|doi=10.1039/js8773200660|title= On some hydrocarbons obtained from the homologues of cinnamic acid; and on anethol and its homologues|url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015077817446;view=1up;seq=1444}}
3. ^{{cite journal |title= The nature of the catalyst in the Perkin condensation |first1= J. F. J. |last1= Dippy |first2= R. M. |last2= Evans |journal= J. Org. Chem. |year= 1950 |volume= 15 |issue= 3 |pages= 451–456 |doi= 10.1021/jo01149a001 }}
4. ^{{cite journal|author=Johnson, J. R.|journal=Org. React.|year=1942|volume=1|pages= 210|doi=10.1002/0471264180.or001.08|title=The Perkin Reaction and Related Reactions|isbn=0471264180}}
5. ^House, H. O. (1972) Modern Synthetic Reactions, W. A. Benjamin, Menlo Park, California, 2nd ed, pp. 660–663
6. ^{{cite journal|author=Rosen, T.|journal=Compr. Org. Synth.|year=1991|volume=2|pages= 395–408|doi=10.1016/B978-0-08-052349-1.00034-2|title=The Perkin Reaction|isbn=978-0-08-052349-1}}
7. ^Bansal, Raj K. (1998) Organic Reaction Mechanisms, Tata McGraw Hill, 3rd Edition , pp. 199–201, {{ISBN|9780470858585}} {{DOI|10.1002/0470858583}}.
8. ^{{cite journal|last1=Solladié|first1=Guy|last2=Pasturel-Jacopé|first2=Yacine|last3=Maignan|first3=Jean|title=A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids|journal=Tetrahedron|volume=59|issue=18|year=2003|pages=3315–3321|issn=0040-4020|doi=10.1016/S0040-4020(03)00405-8}}
{{DEFAULTSORT:Perkin Reaction}}

2 : Condensation reactions|Name reactions

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