Conclusions
-
1.
Dienicδ-dimethylaminocarbonyl compounds were synthesized containing a Br, OEt, or CN substituent in the γ-position.δ-Dimethylamino-γ-cyanodienones are found in the open form and do not cyclize to 2H-pyrans.
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2.
The existence of a dynamic equilibrium was established betweenδ-dimethylamino-γ-bromodienone (orδ-dimethylamino-γ-ethoxydienone) and 3-bromo-2-dimethylaminopyran (or 3-ethoxy-2-dimethylaminopyran), which depends on the solvent and temperature.
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3.
The equilibrium is shifted toward the 2H-pyran with increasing bulk of the solvent in the γ-position of theδ-dimethylaminodienone.
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4.
The 2H-pyrans upon the action of UV light undergo reversible dissociation of the C-O bond and isomerize toδ-aminodienones.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1323–1335, June, 1989.
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Krasnaya, Z.A., Stytsenko, T.S., Bogdanov, V.S. et al. Effect of substituents at the γ-position of δ-dimethylaminodienones on their capacity to cyclize to substituted 2H-pyrans. Russ Chem Bull 38, 1206–1218 (1989). https://doi.org/10.1007/BF00957155
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DOI: https://doi.org/10.1007/BF00957155