Preparation and properties of quaternary ammonium and phosphonium permanganates

Abstract

Trityl bromide was obtained from Aldrich and 6-iodo-l-heptene(1) was prepared from its tosylate and sodium iodide as reported earlier.6 5-Chloro-l-cyclooctene (4), 5-bromo-l-cyclooctene (3), and 5-iodo-l-cyclooctene (2) can be obtained in nearly quantitative yield by Pritzkow's method of adding dry HX to 1,5-cyclooctadiene in CH2C12.13Gas chromatographic analyses were conducted on a Hewlett-Packard Model 700 instrument using a FID detector and packed columns. Quantitative GLC analyses were obtained with the use of response factor corrected peak areas using internal standards.Infrared spectra were recorded on a Perkin-Elmer Model 621 spectrophotometer.Mass spectra were obtained on a Varían MAT 112S, and for EPR studies spectra were recorded on a Varían E 109 ES.General Procedure for Reduction of Alkyl Halides. The appropriate amounts of alkyl halide (0.1 M) and metal hydride (0.2 M) were combined in a reaction tube under N2 in THF and shielded from light. For the EPR study, the reagents were combined in an EPR tube under N2. In those cases where DCPH or DCPD were employed, the additive was added to the metal hydride, followed by the addition of the appropriate alkyl halide. Control experiments showed that no reaction occurred between LiEtgBD and DCPH, as determined by the constancy of the P-H (13) Franz, H.

Structure of tetraethylammonium permanganate

“…The structures of methyltriphenylphosphonium permanganate and n-heptyltriphenylphosphonium permanganate have been reported (Karaman, Barton, Robertson & Lee, 1984). The average Mn---O bond distances in their structures were substantially short [1.47 (2) TETRAETHYLAMMONIUM PERMANGANATE Mn--O bond length in the present structure is 1.610 (6) A which is closer to the reported values for the potassium (Palenik, 1967) and caesium (Prout & Nassimbeni, 1966) …”

Oxidation of hydrocarbons. 17. Solvent and substituent effects on the oxidation of styrene derivatives by quaternary ammonium permanganates

“…Although most salts exist as discrete ions in aqueous solutions, quaternary ammonium compounds when dissolved in organic solvents are more likely to form ion pairs (11). Brandstrom has shown that the probability of salts existing as ion pairs is inversely dependent on the distance between the centres of the two ions and the dielectric constants of the solvents (20).…”

Oxygen transfer reactions. 2. A comparison of the reactions of ruthenium tetroxide, chromyl chloride, and permanganate with thianthrene 5-oxide

“…Benzyltriethylammonium permanganate was prepared by adding a saturated aqueous solution of KMnO, (4.16 g, 0.0264 mol) dropwise to a stirred solution of benzyltriethylammonium chloride (6.00 g, 0.0264 mol) in 100 mL of water (15). The dark purple precipitate that formed was collected under suction and vacuum dried over phosphorus pentoxide.…”