Polar effects in free radical reactions. Homolytic aromatic amination by the amino radical cation,. cntdot.+ NH3: reactivity and selectivity

A Citterio, A Gentile, F Minisci, V Navarrini…

Index: Citterio, Attilio; Gentile, Anna; Minisci, Francesco; Navarrini, Valter; Serravalle, Marco; Ventura, Susanna Journal of Organic Chemistry, 1984 , vol. 49, # 23 p. 4479 - 4482

Full Text: HTML

Citation Number: 31

Abstract

Small amounts of Fe (I1) salt initiate redox chains with hydroxyamino-0-sulfonic acid (HSA) and aromatic compounds leading to the amination of the aromatic ring. The positional and substrate selectivity with a variety of substituted benzenes show the important role of the electrophilic character of the radical.+ NH3. Hammett relationships with u and u+ are roughly observed. The lower sensitivity to polar effects of the radical.+ NH3 compared with (CH3) ...