
TY  - JOUR
A1  - Elson, Kathryn E. 
A1  - Jenkins, Ian D. 
A1  - Loughlin, Wendy A. 
T1  - Cyclic Analogues of the Hendrickson &#8216;POP&#8217; Reagent
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2004
VL  - 57
IS  - 4
SP  - 371
EP  - 376
KW  - dehydration reactions&#8212;Hendrickson reagent&#8212;kinetics&#8212;&#8216;POP&#8217; reagent&#8212;synthesis (org.)
UR  - https://doi.org/10.1071/CH03223 
N2  - 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. 
ER  -

