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Substituent effect on the photochemistry of 4,4-dialkoxylated- and 4-hydroxylated cyclohexenones.
- Source :
-
Tetrahedron . Nov2013, Vol. 69 Issue 46, p9591-9599. 9p. - Publication Year :
- 2013
-
Abstract
- Abstract: Photochemistry of the title compounds in various solvents was studied using a broad band of light centered at 350 nm. C-4 spiroketal cyclohexenone 4 (1.0 M) afforded dimers and 12b with the predominance of the former in polar solvent and the latter in nonpolar solvent. When the concentration was reduced to, 4 underwent solvent addition in nonpolar solvent and ring-contraction in polar solvents. 4,4-Dimethoxycyclohexenones 5a–d in TFE exhibited a different photochemical behavior. The 5-vinyl-substituted enone afforded the bridged-bicyclic ketone 16. Cyclohexenone 5b with methyl moieties at C-2 and C-3 underwent aromatization whereas cyclohexenones with butyl substituent at C-5 and 5d with silylated alcohol at C-2 underwent solvent exchange. In γ-hydroxylated cyclohexenones 6a–c ring-contraction and solvent exchange were observed. Photochemistry of the title compounds from the mechanistic viewpoint is also described. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 69
- Issue :
- 46
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 90510924
- Full Text :
- https://doi.org/10.1016/j.tet.2013.09.037