Chemistry of Heterocyclic Compounds p. 1584 - 1590 (2003)
Update date:2022-08-11
Topics:
Jansone
Fleisher
Andreeva
Leite
Popelis
Lukevics
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.
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