ChemInform Abstract: REACTION OF N‐(P‐TOLUENESULFONYL)‐1,4‐QUINONE MONOIMINES WITH P‐TOLUENESULFINIC ACID

Abstract

Die Reaktion der im Titel genannten Chinonimine (I) und des Naphthochinonimins (IX) mit p‐Toluolsulfinsäure, die nach Verfahren A) in Form ihres Natriumsalzes (II) eingesetzt wird, führt zu Produkten der öJ‐Anlagerung, wie z.B. (IV), (VI), (VIII) und (X), der Lö‐Anlagerung, wie z.B. (VII) und/ oder der öß‐Anlagerung, wie z.B. (V).

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

“…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].…”