2-Phenyl-2-propyl ethers

Write line formulas for (a) dibutyl ether, (b) propyl phenyl ether, and (c) methyl octyl ether. 

Photolysis of Hvdroxy-3-faminoethane thiosulfuric add) propyl phenyl ether (AETSAPPEt. AETSAPPE possesses identical functionality to the thiosulfate group in PATE, but being only monofunctional, AETSAPPE is incapable of forming insoluble polymer upon photolysis. As a result, the reaction products should remain soluble in typical organic solvents, making separation and identification of products possible. 

For the preparation of an aryl alkyl ether there are again two combinations to be considered here, one combination can usually be rejected out of hand. /i-Propyl phenyl ether, for example, can be prepared only from the alkyl halide and the phenoxide, since the aryl halide is quite unreactive toward alkoxides. 

Another mass spectrometric experiment from this laboratory (P.S. Mayer and T.H. Morton, unpublished results) confirms the pathway for decomposition of the covalent oxonium ion shown in Scheme 13 for R=C2H5. Chemical ionization of -propyl phenyl ether with methane reagent gas at... 

Various forms of radiation have been used to produce ions in sufficient quantitites to yield neutral products for subsequent analysis. In principle, it should be possible to use intense beams of UV below ionization threshold for this purpose. To date, however, efforts to collect neutrals from resonant multiphoton ionization (REMPI) have not succeeded. In one experiment, 1 mbar of gaseous -propyl phenyl ether was irradiated at room temperature with a 0.1 W beam of 266 nm ultraviolet (from an 800 Hz laser that gives 8 n pulses) concurrent with a 0.5 W beam at 532 nm. The beams were intense enough not only to ionize the ether in the mass spectrometer, but also to excite it so that it expels propene. After several hours of irradiation < 10% of the starting material remained. Production of carbon monoxide and acetylene (decomposition products of the phenoxy group) could be detected by infrared absorption spectroscopy, but the yield of neutral propene (as measured by NMR spectroscopy) was infinitesimal. 

PhOH, l,8-diazabicyclo[5,4,0]undec-7-ene and CjHtI in ethanol refluxed for 3h., to give n-propyl phenyl ether. 

A mixture of 2-(phenoxymethyl)oxirane, S-phenyl thiobenzoate, and a little Bu4NBr in dry DMF stirred at 110° for 25 h - 2-benzoyloxy-3-(phenylthio)propyl phenyl ether. Y 71% (82.4% conversion). F.e. and with 18-crown-6-metal complexes s. T. lizawa et al., Bull. Chem. Soc. Japan 62, 597-8 (1989) with a polymer-based phosphonium salt cf. Chem. Letters 1988, 1605-8. 

DotelU, G., Gallazzi, M. C., Perfetti, G., Montoneri, E., Proton conduetivity of poIy(dipropyl)phosphazene-snlfonated poly[(hydroxy)propyl, phenyl]ether-H3P04 composite in dry environment. Solid State Ionics, 2005,176, 2819-2827. 

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