A10479 Phenyl phosphorodichloridate, 97%

Phenyl phosphorodichloridate, 97%

Chemische Eigenschaften

Literaturverweise

Reagent for the preparation of phosphate diesters. The phenyl group is removable by hydrogenolysis: J. Am. Chem. Soc., 75, 4510 (1953).

Coupling reagent, e.g. in pyridine for the preparation of derivatives of sulfinic acids with alcohols, amines, thiols etc.: Synthesis, 937 (1980). Similarly, carboxylic acids in pyridine can be coupled with thiols to give thiocarboxylic acid S-esters: Can. J. Chem., 58, 2645 (1980), and with sodium azide in the presence of a phase-transfer catalyst to give acyl azides: Synth. Commun., 13, 289 (1983).

Reacts with the Li enolates of ß-diketones, in the presence of LiCl, to give ß-chloro-ɑß-enones: Can. J. Chem., 64, 520 (1986).

In combination with NaI, cleaves dialkyl ethers to iodides in high yield: Synth. Commun., 18, 119 (1988), and 1,3-dithianes and other dithioacetals to carbonyl groups: Tetrahedron Lett., 29, 5471 (1988).

In combination with Dimethyl­ sulfoxide, A13280, effects selective oxidation of alcohols to aldehydes or ketones with less ɑ-chlorination than the more usual Swern (Oxalyl­ chloride, A18012) system: J. Org. Chem., 52, 5621 (1987). Similarly, benzylamines have been converted to benzaldehydes: Synth. Commun., 19, 3407 (1989).

For a brief feature on uses of the reagent in synthesis, see: Synlett, 1651 (2004).

Kuo, C. W.; Hsieh, M. T.; Gao, S.; Shao, Y. M.; Yao, C. F.; Shia, K. S. Beckmann Rearrangement of Ketoximes Induced by Phenyl Dichlorophosphate at Ambient Temperature. Molecules 2012, 17 (11), 13662-13672.

Nagarkar, A. A.; Crochet, A.; Fromm, K. M.; Kilbinger, A. F. Efficient amine end-functionalization of living ring-opening metathesis polymers. Macromolecules 2012, 45 (11), 4447-4453.