134298-59-2Relevant academic research and scientific papers
Photochemical Reaction of 3-Hydroxy-1-(o-methylaryl)alkan-1-ones: Formation of Cyclopropane-1,2-diols and Benzocyclobutenols through β- and γ-Hydrogen Abstractions
Yoshioka, Michikazu,Miyazoe, Satoru,Hasegawa, Tadashi
, p. 2781 - 2786 (2007/10/02)
Irradiation of 3-hydroxy-2,2-dimethyl-1-(o-methylaryl)-alkan-1-ones 1a-h having a bulky alkyl group or an aryl group on C-3 in methanol gave trans- and cis-cyclopropane-1,2-diols 2a-g and 3a, c-f, h and benzocyclobutenols 4a-h through β- and γ-hydrogen abstractions.Irradiation of 3-hydroxy-2,2-dimethyl-1-(o-methylphenyl)-alkan-1-ones 1i-k having ethyl, methyl or no substituent at C-3 gave benzocyclobutenols 4i-k and 1,3-diketones 5i, j, but no cyclopropane-1,2-diols.The cyclopropane-1,2-diols were sensitive to air and readily oxidized to the corresponding 1,3-diketones.Irradiation of 3-hydroxy-4,4-dimethyl-1-(o-methylaryl)pentan-1-ones 8a, b having a methyl group or no substituent on C-2 gave benzocyclobutenols 9a, b, the peroxide 10 and phthalides 11a, b. 3-Hydroxy-2,2-dimethyl-1,3-diphenylpropan-1-one 12a and 3-hydroxy-2,2,4-trimethylpentan-1-one 12b also underwent photocyclization through β-hydrogen abstraction to give cyclopropane-1,2-diols 13a, b and 14.
Photochemical Reaction of 1-(o-Methylphenyl)-2,2-dimethyl 1,3-Diketones
Yoshioka, Michikazu,Nishizawa, Kaori,Arai, Masayuki,Hasegawa, Tadashi
, p. 541 - 547 (2007/10/02)
The photochemistry of 1-(o-methylphenyl)-2,2-dimethylpropane-1,3-diones 4 has been investigated.Compounds 4a-h underwent photocyclization to give benzocyclobutenols 11a-h and naphthalenones 12a-h in hexane or methanol.Compound 4i gave the naphthalenone 12i in methanol.The product ratio 11:12 was greater in hexane than in methanol.This ratio increases with chain branching of the C-3 substituent R and with increasing size of R.Compounds 4a, b and d gave isobutyrophenones 13a, b and d along with products 11 and 12 in hexane.
