Synthesis of ω-Tritiated and ω-Fluorinated Analogues of the Trail Pheromone of Subterranean Termites

Article abstract of DOI:10.1021/jo00181a023

A series of unsaturated ω-fluoro alcohols have been prepared stereoselectively.These simple compounds are structural analogues of the trail pheromone of termites in the genus Reticulitermes.The toxicity of these ω-fluoro alcohols to R. flavipes is maximal for the C12 alcohols, and the attractiveness of these C12 analogues increases in the order saturated alkanol < (Z)-3-alkenol << (Z,Z)-3,6-alkadienol.Two <12-3H>-12-fluoro alcohols and a <12-3H>-nonfluorinated analogue were prepared to examine the catabolism of the pheromone analogues.