Photoinduced reactions—LVIII

作者: I. Saito , N. Yoshimura , T. Arai , K. Omura , A. Nishinaga

DOI: 10.1016/S0040-4020(01)88932-8

关键词:

摘要: Abstract The photosensitized oxygenation of 4,6-di-t-butylresorcinol (1) and its methyl ethers 8 10 in methanol have been examined. Resorcinol affords ketoester 2 lactone 3. Photosensitized monoethyl ether dimethyl gives hydroperoxide 9 epoxy-ketone 11, respectively; participation singlet oxygen these reactions is demonstrated. A mechanism involving 1,4-cycloaddition to the aromatic nucleus proposed for formation but a phenoxy radical intermediate 14

参考文章(12)
D.I. Crandall, R.C. Krueger, F. Anan, K. Yasunobu, H.S. Mason, Oxygen Transfer by the Homogentisate Oxidase of Rat Liver Journal of Biological Chemistry. ,vol. 235, pp. 3011- 3015 ,(1960) , 10.1016/S0021-9258(18)64580-6
T. Matsuura, H. Matsushima, S. Kato, I. Saito, Photoinduced reactions—LVII Tetrahedron. ,vol. 28, pp. 5119- 5129 ,(1972) , 10.1016/S0040-4020(01)88931-6
Teruo Matsuura, Akira Nishinaga, Naoki Yoshimura, Tetsuzo Arai, Kanji Omura, Hideo Matsushima, Shigeyuki Kato, Isao Saito, Photoinduced reactions. XXXI. Photooxidative ring-cleavage of dihydric phenols as possible models for biological oxygenation Tetrahedron Letters. ,vol. 10, pp. 1673- 1676 ,(1969) , 10.1016/S0040-4039(01)87976-4
Christopher S. Foote, Photosensitized oxygenations and the role of singlet oxygen Accounts of Chemical Research. ,vol. 1, pp. 104- 110 ,(1968) , 10.1021/AR50004A002
William H. Fenical, David R. Kearns, Phillip Radlick, Mechanism of the addition of 1.DELTA.g excited oxygen to olefins. Evidence for a 1,2-dioxetane intermediate Journal of the American Chemical Society. ,vol. 91, pp. 3396- 3398 ,(1969) , 10.1021/JA01040A066
Isao Saito, Shigeyuki Kato, Teruo Matsuura, Photoinduced reactions. XL addition of singlet oxygen to monocyclic aromatic ring Tetrahedron Letters. ,vol. 11, pp. 239- 242 ,(1970) , 10.1016/0040-4039(70)80035-1
Teruo Matsuura, Naoki Yoshimura, Akira Nishinaga, Isao Saito, Photoinduced reactions. XXX. Hydrogen abstraction from a phenol by singlet oxygen Tetrahedron Letters. ,vol. 10, pp. 1669- 1671 ,(1969) , 10.1016/S0040-4039(01)87975-2
Isao Saito, Teruo Matsuura, Photoinduced reactions. XLIV. Reactivity of singlet oxygen toward methoxybenzenes. Tetrahedron Letters. ,vol. 11, pp. 4987- 4990 ,(1970) , 10.1016/S0040-4039(00)89327-2
Harry H. Wasserman, John R. Scheffer, Singlet oxygen reactions from photoperoxides. Journal of the American Chemical Society. ,vol. 89, pp. 3073- 3075 ,(1967) , 10.1021/JA00988A064