1028307-99-4Relevant academic research and scientific papers
Regioselective 1,4-addition of ammonia to 1-arylalka-1,3-dienes and 1-aryl-4-phenylbuta-1,3-dienes by photoinduced electron transfer
Kojima, Ryuji,Yamashita, Toshiaki,Tanabe, Kimiko,Shiragami, Tsutomu,Yasuda, Masahide,Shima, Kensuke
, p. 217 - 222 (2007/10/03)
The photoamination of 1-arylalka-1,3-dienes 1a-f and 1-aryl-4-phenylbuta-1,3-dienes 1g-k with NH3 in the presence of p-dicyanobenzene (DCB) gives 4-amino-1-arylalk-2-enes 2a-f and 1-amino-1,4-diarylbut-2-enes 2g-k, respectively. The photoamination proceeds by nucleophilic addition of NH3 to the cation radicals of 1+. generated by photoinduced electron transfer to DCB. The regiochemistry of 2 is related to the distribution of the positive charge in 1+. calculated by the PM3-UHF/RHF method, the stability of the aminated radicals formed by the addition of NH3 to 1+. and the stability of the aminated anion formed by the reduction of the aminated radicals by DCB-.. The stabilities of these intermediates are estimated by the calculation of the heat of formation by the PM3-UHF/RHF method. Distributions of the positive charge in 1+. and the stabilities of the aminated anion show a good agreement with the product analysis.
