A novel, selective free-radical carbamoylation of heteroaromatic bases by Ce (IV) oxidation of formamide, catalysed by N-hydroxyphthalimide

F Minisci, F Recupero, C Punta, C Gambarotti…

Index: Minisci, Francesco; Recupero, Francesco; Punta, Carlo; Gambarotti, Cristian; Antonietti, Fabrizio; Fontana, Francesca; Pedulli, Gian Franco Chemical Communications, 2002 , # 21 p. 2496 - 2497

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Citation Number: 22

Abstract

We have also evaluated the bond dissociation energy of the O–H bond in NHPI (88.1 kcal mol −1 ) and the absolute rate constants for hydrogen abstraction from NHPI by the peroxyl radical (7.4 × 10 3 M −1 s −1 at rt, the rate being much higher with alkoxy radical for obvious enthalpic reasons) and from the benzylic C–H bond of cumene by the PINO radical (6.1 M −1 s −1 at rt). 4–6 The PINO radical is much more reactive than the TEMPO radical in hydrogen ...