52498-15-4Relevant academic research and scientific papers
Synthesis of cyclobutane lignans via an organic single electron oxidant-electron relay system
Riener, Michelle,Nicewicz, David A.
, p. 2625 - 2629 (2013)
A direct method to synthesize lignan cyclobutanes and analogs via photoinduced electron transfer is presented. A variety of oxygenated alkenes are employed to furnish terminal or substituted cyclobutane adducts with complete regiocontrol, yielding cycload
Visible-Light-Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives
Wang, Leifeng,Wu, Fengjin,Chen, Jiean,Nicewicz, David A.,Huang, Yong
, p. 6896 - 6900 (2017/06/08)
We report a formal [4+2] cycloaddition reaction of styrenes under visible-light catalysis. Two styrene molecules with different electronic or steric properties were found to react with each other in good yield and excellent chemo- and regioselectivity. This reaction provides direct access to polysubstituted tetralin scaffolds from readily available styrenes. Sophisticated tricyclic and tetracyclic tetralin analogues were prepared in high yield and up to 20/1 diasteroselectivity from cyclic substrates.
Effect of co-adsorbed water on photodimerization and photooxygenation of 4-methoxystyrene included in NaY
Matsubara, Chie,Kojima, Masanobu
, p. 3439 - 3442 (2007/10/03)
Irradiation of 4-methoxystyrene (1) in zeolite NaY under vacuum, dry oxygen, and wet air yielded dimers and oxygenation products dependent on the atmosphere and co-adsorbed water. Head-to-head cis- and trans-cyclobutane dimers of 1 were produced at the isomer ratio of 91/9 under vacuum through excimer of 1 and 38/62 under wet air through cation radical of 1, respectively. However, 4-methoxybenzaldehyde was a primary product under dry oxygen at the expense of production of the dimers (c/t = 81/19). These results show significant differences in the photochemical behavior of 1 in solution and in NaY.
Nanosecond and picosecond dynamics of the radical cation mediated dimerization of 4-methoxystyrene
Schepp,Johnston
, p. 6895 - 6903 (2007/10/02)
The addition of the 4-methoxystyrene radical cation to neutral 4-methoxystyrene and the cleavage reactions of the 1,2-bis(4-methoxyphenyl)cyclobutane radical cation in acetonitrile have been studied by product analysis and by nanosecond and picosecond tra
Dye-Sensitized Oxygenation and Dimerization of 4-methoxystyrene through Electron Transfer
Kojima, Masanobu,Kuriyama, Yasunao,Sakuragi, Hirochika,Tokumaru, Katsumi
, p. 2724 - 2729 (2007/10/02)
Photoreactions of 4-methoxystyrene (1) sensitized with dyes such as Acriflavine, Rhodamine 6G, and Methylene Blue in methanol under oxygen afforded 4-methoxybenzaldehyde, its dimethyl acetal, and 2-methoxy-2-(4-methoxyphenyl)ethanol as oxidation products together with the corresponding dimers, cis- and trans-cyclobutanes in a ratio of cis/trans ca. 5/95.On the basis of quenching studies of fluorescence and T-T absorption of the dyes, the oxygenation and dimerization are proposed to proceed through an electron transfer from 1 to excited singlet dyes but not to involve generation of singlet oxygen.
MECHANISTIC CONSIDERATIONS ON PHOTOREACTION OF ORGANIC COMPOUNDS VIA EXCITATION OF CONTACT CHARGE TRANSFER COMPLEXES WITH OXYGEN
Onodera, Kazuyuki,Furusawa, Gen-ichi,Kojima, Masanobu,Tsuchiya, Masahiro,Aihara, Shin,et al.
, p. 2215 - 2220 (2007/10/02)
Reactions of various organic compounds induced by excitation of their contact charge transfer (CCT) pairs with oxygen were classified into three types of behaviour on the basis of reaction products.It is proposed that the excited state of the CCT pairs gives the products through the most isoenergetic course along the plausible exothermic pathway.
Photochemical Electron-transfer Reaction between Aromatic Olefins and Metal Ions. Dependence of the Reaction Course on the Structure of the Olefins
Kojima, Masanobu,Sakuragi, Hirochika,Tokumaru, Katsumi
, p. 521 - 524 (2007/10/02)
To investigate the photochemical electron transfer from aromatic olefins to copper(II) or iron(III) ions, a series of substituted styrenes (1) was irradiated in the presence of copper(II) or iron(II) salts in methanol, which gave dimethoxylated monomers (2) and one or more of three types of dimethoxylated dimers .The formation of these products are reasonably attributed to the participation of hte cation radicals of the olefins generated by electron transfer from excited olefins to the methal ions.Substituents on the substrates are found to govern the reaction products.
THE ROLE OF OXYGEN AS AN ELECTRON ACCEPTOR IN DIMERIZATION OF SOME STYRENE DERIVATIVES
Kojima, Masanobu,Sakuragi, Hirochika,Tokumaru, Katsumi
, p. 2889 - 2892 (2007/10/02)
Irradiation of the CT bands of p-methoxy- and p-methylstyrene with oxygen induced the dimerization of the olefins through their cation radicals generated by electron transfer on CT excitation.
