Reaction of arenediazonium tetrafluoroborates with 3-(allyloxy)propane-1,2-diol and 2,2-bis(allyloxymethyl)butan-1-ol in the presence of thiocyanates

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.Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 12, 2004, pp. 2019–2022.Original Russian Text Copyright © 2004 by Grishchuk, Baranovskii, Kovalskii, Gorbovoi.This revised version was published online in April 2005 with a corrected cover date.