AQsfract:
The photoaminations of trans-1-arylpropenes (aryl = 2-methoxyphenyl (1). 3methoxyphenyl (2). 3.4-dimethoxyphenyl (3). and 4-methoxyphenyl (4)) with NH3. i-PrNH2, and t-BuNH2 (RNH2) in the presence of p-dicyanobenxene @-DCB) gave 2-alkylamino-I-arylpropanes (9) and/or 2-alkylamino-I-aryl-I-(4-cyanophenyl)propanes (10). The photoaminations of 1,2dihydro-7methoxynaphthalenes (6-8) with RNH2 in the presence of p-DC9 gave mainly 2-alkylamino-l-(4cyanophenyl)-6-methoxy-1,2.3,4-tetrahydronaphthaJenes (13). The photoamination of truns-l-(3.5dimethoxyphenyl)propene (5) with i-RNH2 occurred at aromatic ring to give rranr-I-(2~isopropylamino-3.5-dimethoxyphenyl)propene (11). The photoaminations of l-4 and 6-8 with NH3 in the presence of m-dicyanobenzene gave the aminated products without incorporation of cyanophenyl group. Furthermore, the addition of 1.3.5~triphenylbenzene and m-terphenyl for these reactions improved the yields of the photoaminated products. 12d 9 (1:l) 13d 41 (1:O) 83 51 13e 76 (1:O) 24 131 50 (1:O) 36 13g 18 (1:0) 88 59 u Irradiation of an ammonia-saturated MeCN-Hz0 (9:l; 70 ml) solution comaining l-4,6-8 (3.5 mmol). p-LXX (3.5 mmol), or a deaerated MeCN solution (70 ml) containing 4-7 (3.5 mmol), p-DCB (3.5 mmol). and the amine (17.5 mmol). * Oxidation potentials vs. Ag/NO3. c Isolated yields based on the consumed substrates. The values in parenthesis are isomer ratio. d Aher the photoreaction, l-4 were recovered as cis and wanr-isomers.