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Radical cyclization

3 real reactions from the literature, on primary alkyl bromides, vinyl bromides and tertiary alkyl chlorides. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Radical cyclization: bromomethyl-dimethyl-(3-methylbut-2-enoxy)silane (a primary alkyl bromide) with AIBN; SnBu3H gives 2,2-dimethyl-4-propan-2-yloxasilolane (the cyclized product). 71% yield.

    Radical cyclizationJ. Org. Chem. 2016, 81, 8544
  2. Radical cyclization: a vinyl bromide with SnBu3H; AIBN gives 1-methyl-3-propan-2-yl-2-prop-1-ynylcyclopentene (the cyclized product). 85% yield.

    Radical cyclizationJ. Org. Chem. 1990, 55, 2983
  3. Radical cyclization: N-(2,2,2-trichloro-1-phenylethyl)prop-2-en-1-amine (a tertiary alkyl chloride) with SnBu3H; AIBN gives 3,3-dichloro-4-methyl-2-phenylpyrrolidine (the cyclized product). 79% yield.