New N-acetyl-1,4-benzoquinone monoimines alkyl-substituted in the quinoid ring were synthesized. The hydrohalogenation of N-acetyl(aroyl)-1,4-benzoquinone monoimines proceeds exclusively in keeping with the 1,4-addition. The hydrochlorination occurs along the ionic mechanism, in the hydrobromination grows the role of the radical mechanism.

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Hydrohalogenation of N-[arylsulfonylimino(phenyl)methyl]-2,5(3,5)-dimethyl-1,4-benzoquinone monoimines follows exclusively the 1,4-addition pattern, whereas N-[arylsulfonylimino(phenyl)methyl]-2,6-dimethyl-1,4-benzoquinone monoimines take up hydrogen halides according to the 6,3-addition scheme. Ar = Ph (a), 4-MeC 6 H 4 (b), 4-ClC 6 H 4 (c); I, IV, VII, X, XIII, R 1 = R 2 = Me; II, V, VIII, XI, XIV, R 1 = i-Pr, R 2 = Me; III, VI, IX, XII, XV, R 1 = Me, R 2 = i-Pr; IV-VI, X-XII, Hlg = Cl; VII-IX, XIII-XV, Hlg = Br.

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