The cathodic cleavage of the nitrobenzenesulfonyl group from aliphatic amines in N, N-dimethylformamide

摘要: Abstract The reduction of benzenesulfonyl derivatives n-butylamine and N,N -di-n-butylamine with nitro substituents at the 2, 3 4 positions phenyl ring in -dimethylformamide is reported. N , -di-n-butyl-4- -n-butyl-2-nitrobenzenesulfonamides are reduced two cathodic steps. first one, about −0.90 V vs. SCE, a reversible one-electron process, gives stable anion radical. second step −1.70 SCE leads to cleavage S-N bond good yields ( > 70%). It shown that -n-butyl-3- -n-butyl-4-nitrobenzenesulfonamide different, three occurs formation an unstable radical, which decomposes via N-H cleavage. this sulfonamide −1.16 third arises when remaining radical its dianion. rapid but always minor process. mechanisms discussed.