SYNTHESIS AND PHOTOISOMERIZATION OF 3-CYANO-6,6-DIMETHYL-4-(4-NITROPHENYLVINYL)-5,6-DIHYDROPYRAN-2-ONE

Authors

  • Д. Янсоне Latvian Institute of Organic Synthesis, Riga LV 1006
  • М. Флейшер Latvian Institute of Organic Synthesis, Riga LV 1006
  • Г. Андреева Latvian Institute of Organic Synthesis, Riga LV 1006
  • Л. Лейте Latvian Institute of Organic Synthesis, Riga LV 1006
  • Ю. Попелис Latvian Institute of Organic Synthesis, Riga LV 1006
  • Э. Лукевиц Latvian Institute of Organic Synthesis, Riga LV 1006

Keywords:

3-cyano-6,6-dimethyl-4-(4-nitrophenylvinyl)-5,6-dihydropyran-2-one, 4-nitrobenzaldehyde, 3-cyano-4,6,6-trimethyl-5,6-dihydropyran-2-one, aldol condensation, AM1 semiempirical method, E-Z-photoisomerization

Abstract

The condensation of 4-nitrobenzaldehyde with 3-cyano-4,6,6-trimethyl-5,6-dihydropyran-2-one leads to the formation of a crotonization product and a compound of the Michael adduct type. The main product of the photochemical conversion of (E)-3-cyano-6,6-dimethyl-4-(4-nitrophenylvinyl)-5,6-dihydropyran-2-one is the Z-isomer. Investigation of the photoisomerization of 3-cyano-6,6-dimethyl-4-(4-nitrophenylvinyl)-5,6-dihydropyran-2-one by the semiempirical AM1 method showed that in the ground
state the E-isomer was thermodynamically more stable than the Z-isomer. E-Z-photoisomerization is effected most probably through the lowest excited singlet state S1.

How to Cite
Jansone, D.; Fleisher, M.; Andreeva, G.; Leite, L.; Popelis, J.; Lukevics, E. Chem. Heterocycl. Compd. 2003, 39, 1584. [Khim. Geterotsikl. Soedin. 2003, 1800.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000018335.49120.af

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Published

2003-12-25

Issue

No. 12 (2003)

Section

Original Papers