A mild and catalyst‐free protocol to obtain several 2‐chloromethylpyrrolidines by the use of a commercial solution of sodium hypochlorite is here reported, without the need for a light source. The choice of the solvent revealed to be crucial in the success of the reaction. Mechanistic studies, both experimental and computational, confirmed a radical mechanism, where the deprotonation step, followed by the oxidation of a N ‐centered anion to the corresponding radical, allowed 2‐chloromethylpyrrolidines, by a very fast cyclization, to be obtained. Sodium hypochlorite plays the role of both the oxidant and the chlorine source.
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Scarfiello et al. (2024) studied this question.
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