42455-99-2Relevant academic research and scientific papers
Easy photochemical preparation of 2-dimethylaminophenylfurans, -pyrroles and -thiophenes
Guizzardi, Benedetta,Mella, Mariella,Fagnoni, Maurizio,Albini, Angelo
, p. 9383 - 9389 (2000)
2-(4-N,N-dimethylaminophenyl) heterocycles are smoothly obtained from the photolysis of 4-chloro-N,N-dimethylaniline in acetonitrile in the presence of furan, pyrrole, thiophene and some of their methyl derivatives bearing a free α-position. With 2,5-dimethyl heterocycles the arylation occurs with equal efficiency in the β position. In the case of furan, when the irradiation is carried out in methanol, cis/trans 2-aryl-5-methoxy-2,5-dihydro adducts are obtained. The reaction is rationalized as involving heterolytic cleavage of the C-Cl bond in the triplet state of the aniline. The intermediacy of the thus formed triplet aryl cation explains the observed high regio- and chemo-selectivity of the process. (C) 2000 Elsevier Science Ltd.
