
%0 Journal Article
%A Elson, Kathryn E. 
%A Jenkins, Ian D. 
%A Loughlin, Wendy A. 
%T Cyclic Analogues of the Hendrickson &#8216;POP&#8217; Reagent
%J Australian Journal of Chemistry
%D 2004/04/01
%V 57
%N 4
%P 371-376
%K dehydration reactions&#8212;Hendrickson reagent&#8212;kinetics&#8212;&#8216;POP&#8217; reagent&#8212;synthesis (org.)
%R https://doi.org/10.1071/CH03223
%U https://www.publish.csiro.au/paper/CH03223 
%X The Hendrickson reagent, triphenylphosphonium anhydride trifluoromethanesulfonate, &#8216;POP&#8217; 1, is a powerful dehydrating agent. Five-, six-, and seven-membered cyclic analogues of the &#8216;POP&#8217; reagent 2&#8211;4 have been prepared and their use for ester and amide synthesis investigated. A kinetic comparison of the cyclic analogues 2&#8211;4 revealed that a considerable increase in the rate of esterification could be achieved when the five-membered ring analogue 2 was used, presumably due to the ease of formation of the putative phosphorane intermediate. The rate of ester formation from a primary alcohol using the Hendrickson reagent 1 was shown to be significantly faster when non-polar solvents were employed. 
