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One reaction pathway involved a 1,4-addition of an iodine radical to the conjugated double bond followed by radical cyclization onto the aromatic ring. However, the following results seemed to be against this proposal in our case: (i) cyclization of 3a took place readily in the dark to afford 4a in a similar yield; (ii) addition of benzoquinone did not inhibit the reaction; (iii) although yield remained moderate, the cyclization of (Z)- and (E)- N -2-dimethyl- N -phenylbut-2-enamide was stereospecific affording two distinct diastereomers (cf. Supporting Information). For radical based cyclization to oxindoles, see
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