The reactions of arenediazonium tetrafluoroborates with 3-(allyloxy)propane-1,2-diol and 2,2-bis(allyloxymethyl)butan-1-ol in the presence of the thiocyanate nucleophile were used to obtain 3-(3-aryl-2-thiocyanatopropoxy)propane-1,2-diols and 2-[(allyloxy)methyl]-2-[(3-aryl-2-thiocyanatopropoxy)methyl]-butan-1-ols. Irrespective of reagent ratio, the second allyl fragment of 2,2-bis(allyloxymethyl)butan-1-ol fails to enter thiocyanatarylation. The presence of hydroxy groups in the unsaturated compounds studied render the latter less reactive than allyl derivatives containing no such groups.At present anionarylation reactions of monoallyl derivatives, such as allyl halides [133], allyl ethers [2,4,5], and certain diallyl derivatives, such as diallyl dioxide [6], diallyl disulfide, and diallyl phthalate and isophthalate [7], have been studied. Allyl derivatives are generally less reactive in anionarylation than vinyl derivatives whose double bonds are activated by electron-acceptor groups. Of particular interest in this context are allyl derivatives containing functional groups able to enter addition or substitution reactions. Thus it has been shown that thiocyanatoarylation of allyl glycidyl ether [5] and allyl iodide [3] occurs with preservation of the glycidyl fragment and iodine atom, respectively, whereas certain unsaturated substrates with readily leaving groups react to give 3-arylpropenes [8,9].Allyl alcohol is the only hydroxyl-containing allyl derivative whose chloro-and thiocyanatoarylation reactions have been studied [2]. To assess the effect of hydroxy groups on the capacity of allyl derivatives for thiocyanatoarylation, we chose as objects for study 3-(allyloxy)propane-1,2-diol and 2,2-bis(allyloxymethyl)butan-1-ol. It was found that arenediazonium tetrafluoroborates react with 3-(allyloxy)propane-1,2-diol in the presence of ammonium thiocyanate and a copper catalyst. The reaction involves evolution of the diazo nitrogen and gives rise to 3-(3-aryl-2-thiocyanatopropoxy)propane-1,2-diols I3V in yields of up 20328%. 6 g N 2 BF 4