| Budget Amount *help |
¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 1997: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1996: ¥1,100,000 (Direct Cost: ¥1,100,000)
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| Research Abstract |
Photochemical reactions of ortho-methyl, -ethyl, and -isopropylaryl ketones having a functional group such as carbonyl, hydroxyl, alkoxyl, or acetoxy group on beta-carbon in their side chain have been investigated. The chemical behavior of the photoproducts have also been investigated.
Irradiation of ortho-alkylarylketones with a beta-keto or beta-ester group gave the corresponding benzocyclobutenols in good yields. The pyrolysis of the benzocyclobutenols thus obtained gave benzocyclobutenones.
Ortho-alkylarylketones with a beta-hydroxyl or beta-alkoxyl group underwent photocyclization via beta- or gamma-hydrogen abstraction to give benzocyclobutenols and cyclopropane-1,2-diols or 2-alkoxyclopropanols.
Irradiation of ortho-alkylarylketones with a beta-hydroxyl or beta-acetoxy group gave two diastereomeric benzocyclobutenols, which underwent thermal interconversion.
The acid treatment of benzocyclobutenols formed from ortho-alkylarylketones with a beta-hydroxyl or beta-acetoxy group and two methyl groups on alpha-carbon gave isopropylidenebenzocyclobutenes.
Irradiation of ortho-isopropylarylketones with a hydroxyl group on beta-carbon gave 2,2-dimethylbenzocyclobutenols which underwent stereospecific hydrogen shift from C-2 methyl group to C-1 carbon on thermal conditions to give arylalcohols with ortho-isopropylidene group.
1- (2', 4', 6'-Trialkylphenyl) -2-methyl-1,3-diketones exists in the enol from in solution. The reaction of singlet oxygen with these enolic 1,3-diketones were affected by solvent polarity, and proceeded through two different conformational isomeric perepoxide.
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