SCHEDULED MAINTENANCE
Reactivity of phenolic nucleophiles towards nitroso compounds
Abstract
The reactivities of a series of mono- and poly-phenolic ambident nucleophiles with the ambident electrophile N-methyl-N-nitroso p-toluenesulfonamide (MNTS) were studied. Reaction with the MNTS sulfonyl group afforded the corresponding sulfonic esters, and reaction with the MNTS nitroso group afforded the C nitrosophenol and/or NO. However, the rate of reaction with the nitroso group correlated well with the basicity of the phenolic oxygen atom, suggesting that both the sulfonyl and nitroso groups of MNTS react with phenolates exclusively through this single nucleophilic centre. Similar behaviour in the reaction between ascorbic acid and.2-ethoxyethyl nitrite suggests that in vivo generation of NO from alkyl nitrites may result from their reaction with biological reductones.
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