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Curtius rearrangement

2 real reactions from the literature, on acid chlorides and anhydrides. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Curtius rearrangement: dodecanoyl chloride (an acid chloride) with 1) NaN3, H2O, acetone; 2) benzene, Δ gives undecyl isocyanate (the isocyanate or amine).

  2. Curtius rearrangement: an anhydride with 1) NaN3, H2O / toluene; 2) Δ (Curtius); 3) HCl, H2O; 4) NaOH gives 1-phenylcyclopentylamine (the isocyanate or amine).