Abstract
1. Facile nucleophilic substitution of bromine in 2-bromoethyldiazoacetate by iodine under the action of Nal in acetone at 20°C was observed with formation of 2-iodoethyl-diazoacetate in 76% yield. Reaction of 2-bromoethyldiazoacetate with KF, KCN, and NaSEt under various conditions lead only to decomposition products of the initial diazoester. 2. Thermocatalytic decomposition of 2-iodoethyldiazoacetate under the action of Cu and CuSO4 at 110°C or Rh(OAc)2 at 25°C has carbene character and in the presence of unsaturated alicyclic compounds leads to the corresponding esters of cyclopropanecarboxylic acids with the yield of 55%.
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