By R. I. Zhdanov (auth.), Professor Dr. Renat I. Zhdanov (eds.)
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I CH3 o +/H ~X I. o XLI Ph X- CH 3 J+I OCHzCHzN-Ph 0", .... Ph N I. o Ph '_' NH NO z ""- X = CL04 , BF4 , CL FeCl 4 ,5bCl 6 , 5nCl~- XLII +/OH ~X x- I. 1. Zhdanov Electrophilic substitution gives radicals containing a quaternary ammonium group. One example of such a reaction was the synthesis of radical XLI [62]. In tetramethylimidazolinoxyls the electrophilic attack may be directed to the nitrogen atom in position 3, for instance, in the interaction with mineral acids and metal halides, with the formation of paramagnetic salts XLII [163].
O XXXVII 0 0 II II • ClCH2CHH2NHCCH2C~ JCH 2CHH 2NHCCH 2J II ClCH2 CCl II 0 N N XXXVIII XXXIX I. 0 Scheme 8 I. 0 Nitroxyl Radicals and Non-Radical Reactions of Free Radicals 39 The number of such reactions of has been considerable, particularly because of the accessibility of the amino radical of the pyrrolidine series XXXIV [157]. Electrophilic substitution in nitroxyl XXXIV with trifluoroacetyl derivatives of amino acids gave radicals XXXV. The protective group was removed with ammonia solution and this led to radicals XXXVI, (n = 1,2,5,10) [160] (Scheme 8).
Br N CXLlIl 0 ONH2 6 . N N=C=O N i. a eXLVI HO Bt)° - Br B n °Br HOO 0B i ta Br Br Br Br N-N-N-N-N a t1sr i. a i. a I. a CXLVII i. a i O' :ex Br' eOOH N i. a Scheme 25 Nitroxyl Radicals and Non-Radical Reactions of Free Radicals 57 dibromocyclopropanone derivative CXLVII, which is then transformed into the corresponding acid CXLVI [231] (Scheme 25). The main products isolated in the reaction of iodine with an alkaline solution of nitroxyl radical I were 3-carboxy- or 3-carbamido-derivatives of 2,2,6,6-tetramethylpyrrolidinoxyl, depending on whether potassium hydroxide or ammonium hydroxyl were used as the alkali [53,54] (Scheme 26).