Abstract
Mechanistic studies of the deoxygenation of primary alcohols by Mitsunobu displacement with o-nitrobenzenesulfonylhydrazine (NBSH) reveal that the monoalkyl diazene intermediates formed in this process are exceedingly good hydrogen-atom donors toward alkyl radicals, exceeding tri- n-butyltin hydride in reactivity. Competition experiments are described wherein the radical intermediates are trapped by intra- and intermolecular addition to carbon-carbon double bonds, to dioxygen, and to the free radical 2,2,6,6-tetramethylpiperidine- N-oxyl (TEMPO).
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