ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The deprotonation reaction mechanism of methyl diethylphosphonoacetate in the presence of lithium salts and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was examined by infrared spectroscopy. It was found that the intermediate species formed by chelation of the bidentate phosphonate with a lithium cation or an ion pair of the salt deaggregated by DBU takes part in the reaction path. The role of the anion X- is to induce the elimination of a protonated DBUH+X- ion pair and that of the solvent is to compete with the bidentate phosphonate in cation solvation. A similar mechanism via a related intermediate is proposed to interpret the results obtained by other workers on the catalysis by Ba(OH)2 of the Wittig-Horner reaction.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610031108
