Efficient monoacetal formation, unprecedented β-cleavage in caged cyclobutyl ketones and dual epimerization of 1,4-diones in the photochemistry of hexacyclo[10.2.1.02,11.04,9.04,14.09,13]pentadeca-5,7-diene-3,10-dione and related systems in alcoholic solvents
- 1 January 1990
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 2,p. 107-110
- https://doi.org/10.1039/c39900000107
Abstract
Irradiation of the title compound and related caged cyclobutyl diones in alcoholic solvents at 300 nm furnishes good yields of monoacetals and leads to products arising from β-cleavage and dual epimerization.Keywords
This publication has 23 references indexed in Scilit:
- Baeyer-Villiger oxidation of hexacyclo[10.2.1.02,11.04,9.04,14.09,13]pentadeca-3,10-dione systemsThe Journal of Organic Chemistry, 1989
- ⊼-Facial Stereoselectivity in Diels-Alder Reaction of Hexacyclo [7.4.2.01,9.03,7.04,14.06,15] Pentadecane-10,12-diene-2,8-dioneSynthetic Communications, 1989
- .pi.-Facial selectivity in Diels-Alder reactions of hexacyclo[10.2.1.02,11.04,9.04,14.09,13]pentadeca-5,7-diene-3,10-dioneThe Journal of Organic Chemistry, 1987
- Photochemie von 1‐Methoxybicyclo[2.2.2]octenonen; photolytische Cyclopropanspaltung der primär gebildeten Tricyclo[3.3.0.02,8]octan‐3‐oneAngewandte Chemie, 1985
- Photochemistry of 1-Methoxybicyclo[2.2.2] octenones; Photolytic Cyclopropane Cleavage of the Initially Formed Tricyclo [3.3.0.02,8]octan-3-onesAngewandte Chemie International Edition in English, 1985
- A photochemical approach to methyl-substituted 5-oxabicyclo[2.1.0]pent-2-enes (Dewar furans)Journal of the Chemical Society, Chemical Communications, 1984
- Synthesis of New Heptacyclic PropellanesBulletin of the Chemical Society of Japan, 1977
- Photoisomerization of conjugated cyclopropyl ketonesJournal of the American Chemical Society, 1970
- Structure and reactivity in the vapor-phase photolysis of ketones. V. Aliphatic cyclopropyl and olefinic ketonesJournal of the American Chemical Society, 1967
- 586. Photochemical cyclisation of diels–alder adductsJournal of the Chemical Society, 1964