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HMPA is the oxide of the highly basic tertiary phosphine hexamethylphosphorous triamide (HMPT), P(NMe2)3. Like other phosphine oxides (such as triphenylphosphine oxide), the molecule has a tetrahedral core and a P=O bond that is highly polarized, with significant negative charge residing on the oxygen atom.
Compounds containing a nitrogen-phosphorus bond typically are degraded by hydrochloric acid to form a protonated amine and phosphate.
It dissolves alkali metals forming blue solutions which are stable for a few hours.Solvated electrons are present in these blue solutions.
^Luehrs, Dean C.; Kohut, John P. (1974). "Hexamethylphosphoramide solvates of alkali metal salts". Journal of Inorganic and Nuclear Chemistry. 36 (7): 1459-1460. doi:10.1016/0022-1902(74)80605-6.
^Gremmo, Norberto; Randles, John E. B. (1974). "Solvated electrons in hexamethylphosphoramide. Part 1.--Conductivity of solutions of alkali metals". Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases. 70: 1480-1487. doi:10.1039/F19747001480.
^Lo, Chi-Chu; Chao, Pei-Min (1990). "Replacement of carcinogenic solvent HMPA by DMI in insect sex pheromone synthesis". Journal of Chemical Ecology. 16 (12): 3245-3253. doi:10.1007/BF00982095. PMID24263426.
^McDonald, Chriss E.; Ramsey, Jeremy D.; Sampsell, David G.; Butler, Julie A.; Cecchini, Michael R. (2010). "Tripyrrolidinophosphoric Acid Triamide as an Activator in Samarium Diiodide Reductions". Organic Letters. 12 (22): 5178-5181. doi:10.1021/ol102040s. PMID20979412.
^Berndt, Mathias; Hölemann, Alexandra; Niermann, André; Bentz, Christoph; Zimmer, Reinhold; Reissig, Hans-Ulrich (2012). "Replacement of HMPA in Samarium Diiodide Promoted Cyclizations and Reactions of Organolithium Compounds". European Journal of Organic Chemistry. 2012 (7): 1299-1302. doi:10.1002/ejoc.201101830. ISSN1099-0690. Tripyrrolidinophosphoric acid triamide (TPPA) can replace carcinogenic HMPA as a Lewis basic additive in many reactions involving samarium ketyls. In most cases, yields and selectivities of cyclizations of (het)aryl, alkenyl, and alkynyl ketones are similar.