133708-95-9Relevant academic research and scientific papers
Controlling the photochemical reactions of alkenes by light-path length effects of a microchannel reactor
Yamashita, Toshiaki,Matsushita, Shuhei,Nagatomo, Takuya,Yamauchi, Ryosuke,Yasuda, Masahide
, p. 111 - 126 (2013/02/25)
Photoirradiation of Me2CO-H2O solution of pent-4-en-1-ol (1a) with a high-pressure mercury lamp in a test tube gave 8-hydroxyoctan-2-one (3a) in 66 % yield along with oxetane (4a) and the isomer (4a') in 10 % yield. Irradiation of the running Me2CO-H2O solution of 1a in the flow system of a microchannel reactor (MCR) gave mainly 4a. The photoreaction of 1,1-diphenylethene (2a) with triethylamine gave a Markovnikov-type adduct (5a) and an anti-Markovnikov-type adduct (6a). The use of the MCR enhanced the production of 5a. These phenomena were explained by the light-path length effects of the MCR.
Photoinduced Nucleophilic Addition of Ammonia and Alkylamines to Aryl-Substituted Alkenes in the Presence of p-Dicyanobenzene
Yamashita, Toshiaki,Shiomori, Koichiro,Yasuda, Masahide,Kensuke, Shima
, p. 366 - 374 (2007/10/02)
The photoamination of 1,1-diphenylpropene (1a) with ammonia and some primary alkylamines in the presence of p-dicyanobenzene gave the corresponding N-substituted 2-amino-1,1-diphenylpropane (2a-e) along with the formation of 3-methyl-4,4-diphenylbutanenitrile (3a), 1,1-diphenylpropane (4a), 3,3-diphenylpropene (5), and diphenylmethane (6).In the case of 1,1-diphenylethene (1b), N-substituted 1-amino-2,2-diphenylethane (2f-h), 4,4-diphenylbutanenitrile (3b), and 1,1-diphenylethane (4b) were produced.In photoamination with t-butylamine in acetonitrile, 3a and 3b were mainly formed as a consequence of the incorporation of acetonitrile to 1a and 1b.The photoamination of 1-phenyl-3,4-dihydronaphthalene (1c) with isopropylamine or t-butylamine gave cis- and trans-N-substituted 1-phenyl-2-amino-1,2,3,4-tetrahydronaphthalenes (15 and 16) in a ratio of ca. 8:2.The mechanism of photoamination is discussed in terms of a photochemical electron transfer of 1 to p-dicyanobenzene followed by a nucleophilic addition of the amine to the cation radical of 1.
