Hexamethylphosphoramide
- 1 December 1967
- journal article
- review article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 6 (12), 1046-1067
- https://doi.org/10.1002/anie.196710461
Abstract
Growing interest is being shown in the role of the solvent (particularly polar solvents) in chemical reactions[1–4]. The most remarkable polar aprotic solvent appears to us to be the hexamethylated triamide of orthophosphoric acid, OP(N(CH3)2)3, which is known as hexamethylphosphoramide or tris(dimethylamino)phosphine oxide. Hexamethylphosphoramide[5–7] has recently been studied with respect to its solvent properties for gases[5], for many organic and inorganic salts[7], and for polymers[5], as well as its use as a polymerization co‐catalyst. However, these aspects are not considered in the present paper, which deals with the physical and chemical properties of hexamethylphosphoramide, and in particular with its use as a reaction medium. Our own work on hexamethylphosphoramide began in 1961, and until then very little work had been done on this compound. Even in a paper published by Parker[1b] in 1965, very little reference is made to hexamethylphosphoramide.This publication has 62 references indexed in Scilit:
- Ionisation von BenzylmagnesiumchloridAngewandte Chemie, 1965
- LITHIUM-AMMONIA REDUCTION OF α,β-UNSATURATED KETONES. II. FORMATION AND ALKYLATION OF A β-CARBANION INTERMEDIATEJournal of the American Chemical Society, 1961
- THREE MEMBERED RINGS. II. THE STEREOSELECTIVE FORMATION OF DIFUNCTIONAL CYCLOPROPANESJournal of the American Chemical Society, 1960
- Specific Solvent Effects in the Alkylation of Enolate Anions. I. The Alkylation of Sodiomalonic Esters with Alkyl HalidesJournal of the American Chemical Society, 1960
- STEREOCHEMISTRY OF THE LITHIUM-AMMONIA REDUCTION OF α,β-UNSATURATED KETONESJournal of the American Chemical Society, 1960
- CHEMISTRY OF ENOLATES. IV. SOLVENTS FOR ENHANCED CARBANION ACTIVITY1Journal of the American Chemical Society, 1960
- The Effect of Solvent on Spectra. I. A New Empirical Measure of Solvent Polarity: Z-ValuesJournal of the American Chemical Society, 1958
- A Linear Phosphoryl Absorption RelationshipJournal of the American Chemical Society, 1954
- The Mechanism of the Alkylation of Paraffins. III. The Reaction of Isobutane with 2-Chloro-4,4-dimethylpentane, 3-Chloro-5,5-dimethylhexane and 2- and 3-Chloro-3,4,4-trimethylpentaneJournal of the American Chemical Society, 1953
- Inorganic Oxychlorides as Hydrogen Bonding SolventsJournal of the American Chemical Society, 1941