Reactions of N-substituted 2,6(3,5)-dialkyl-1,4-benzoquinone imines with arenesulfinic acids

Reactions of N-aryl(methyl, trifluoromethyl)sulfonyl-1,4-benzoquinone monoimines with sodium sulfinates

“…Quinone monoimines with the quinoid ring having free positions 2 and/or 6 react with sodium arylsulfi nates as a rule regiospecifi cally providing products of 1,4-addition [6][7][8]. In reactions of N-4-(methylphenyl)sulfonyl-1,4-benzoquinone monoimine [6] and its 2,5-dimethyl- [7] and 3,5-dimethyl derivatives [8] formed up to 15% of the products of 1,6-and 6,1-addition. In the case of N-arylsulfonyl-2,6-dialkyl-1,4-benzoquinone monoimines the reaction course is mainly governed by the steric factor: the volume of the substituents in the positions 2 and 6 of the quinoid ring [8].…”

“…The alkyl substituents in the quinoid ring notably affect the reaction course [5][6][7][8][9]. Quinone monoimines with the quinoid ring having free positions 2 and/or 6 react with sodium arylsulfi nates as a rule regiospecifi cally providing products of 1,4-addition [6][7][8]. In reactions of N-4-(methylphenyl)sulfonyl-1,4-benzoquinone monoimine [6] and its 2,5-dimethyl- [7] and 3,5-dimethyl derivatives [8] formed up to 15% of the products of 1,6-and 6,1-addition.…”

“…This choice of conditions is due to the higher reactivity towards nucleophiles of N-trifl uoromethylsulfonyl-1,4-benzoquinone monoimines IIa-IIf: they react at room temperature and even at cooling [3], in contrast to formerly studied N-arylsulfonyl-1,4-benzoquinone monoimines whose reactions with arylsodium sulfi nates proceed only in boiling acetic acid [5][6][7][8][9].…”

“…The reactivity of N-arylsulfonyl-1,4-benzoquinone monoimines towards sodium arylsulfi nates is suffi ciently well investigated [5][6][7][8][9]. The alkyl substituents in the quinoid ring notably affect the reaction course [5][6][7][8][9].…”

“…The alkyl substituents in the quinoid ring notably affect the reaction course [5][6][7][8][9]. Quinone monoimines with the quinoid ring having free positions 2 and/or 6 react with sodium arylsulfi nates as a rule regiospecifi cally providing products of 1,4-addition [6][7][8].…”