Abstract
The redox reactivity of the two quinoline-5,8-dione derivatives—2-methyl-5,8-dioxo-5,8-dihydroquinoline-7-amine (2a) and N-(2-methyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acet-amide (2b)—has been demonstrated by their reaction with negatively charged three-coordinated phosphorus nucleophiles, such as R2P-YM (1a–d, Y = O or lone pair; R = Ph, tBu, OCH2CMe2CH2O, or EtO; M = Li or Na). 1a–d participated in single-electron transfer (SET) to 2a and 2b, generating the radical anions 3 and 4, respectively, together with short-lived phosphorus-centered radical intermediates of type R2P(= Y)· (5). The radicals 5 dimerize to give R2P(Y)–(Y)PR2 (6). Both 3 and 4 are remarkably persistent with half-lives of more than 1 month in THF (tetrahydrofuran) at 300 K.
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