13 C Labelling experiments show that the title reaction takes place by a free radical mechanism which involves (i) homolysis of the C(3)–alkyl bond, (ii) rearrangement of the resulting 3-indolyl radical to a 3-indolylmethyl radical [e.g., (7)], (iii) ring expansion by competitive neophyl rearrangement or attack at the carbonyl position, and (iv) aromatisation by loss of a hydrogen atom.
H. McNab, J. Chem. Soc., Chem. Commun., 1990, 543 DOI: 10.1039/C39900000543
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