93571-56-3Relevant 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 β-Hydroxyketones. Formation of Cyclopropane-1,2-diols
Yoshioka, Michikazu,Miyazoe, Satoru,Hasegawa, Tadashi
, p. 418 - 419 (2007/10/02)
Irradiation of 3-hydroxy-1-(o-methylaryl)-2,2,4-trimethylpentan-1-ones 1 in methanol gave cyclopropane-1,2-diols 2, 1,3-diketones 3 and benzocyclobutenols 4.
Preparation of Benzocyclobutenones via the Photochemical Cyclization of 1-(ortho-Alkylary)-2,2,4-trimethylpentane-1,3-diones
Yoshioka, Michikazu,Momose, Shinobu,Nishizawa, Kaori,Hasegawa, Tadashi
, p. 499 - 503 (2007/10/02)
Irradiation of 1-(ortho-methylaryl)- and 1-(ortho-ethylaryl)-2,2,4-trimethylpentane-1,3-diones 4a-g in hexane gave benzocyclobutenols 10a-g.However, irradiation of 1-(ortho-isopropylaryl)-2,2,4-trimethylpentane-1,3-diones 4i and 4j resulted in no reaction.Irradiation of 1-mesityl-2,2,4-trimethylpentane-1,3-dione 4h gave a complex mixture of products.Pyrolysis of benzocyclobutenols 10a, b, d-f gave benzocyclobutenones 11a, b, d-f and 2,4-dimethylpentan-3-one 2, whereas that of the benzocyclobutenols 10c, g gave the starting 1,3-diketones 4c, g predominantly along with small amounts of benzocyclobutenones 11c, g and the dimethylpentanone 2.
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.
