Radical merry-go-round: A highly efficient metal-free transformation of phenols into benzamides is designed through one-step conversion of phenols to aryl thiocarbamates and a subsequent radical addition/rearrangement/fragmentation cascade. Computational analysis fully rationalizes the experimentally observed selectivity. Despite the possible competition from NC fragmentation and N-neophyl rearrangement, the transformation exclusively follows the most kinetically and thermodynamically favored O-neophyl rearrangement path.
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Baroudi et al. (2010) studied this question.
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