upon solubility and/or reactivity of the alkyl iodide but there was always maintained at least a tenfold excess of iodo compound to PAT. The sealed ampoules were wrapped in aluminum foil to exclude light and placed in an oil bath maintained at 60.0 ±0.1°f or 4 hr, after which time the ampoules were removed and opened, and an appropriate external standard for glpc analysis was added.The yields of iodobenzene and bromobenzene were determined by glpc employing a Hewlett-Packard F&M Model 700-231 gas chromatograph equipped with thermal conductivity detectors.The analyses were conducted utilizing 6 ft X V* in. columns with liquid-phase packing of SE-30, Carbowax 20M, or FFAP on Chromosorb W, 60-80 mesh. Areas under the peaks were determined by tracing with a planimeter and a correction was applied to the areas obtained to account for the difference in detector sensitivity to iodobenzene and bromobenzene. The relative rates were calculated from eq 3 and reported in Table I.
Summary:The reaction of propylene with formaldehyde in acetic acid solution catalyzed by sulfuric acid is studied . The optimum mole ratio of sulfuric acid to formaldehyde is found to be about 0.2 and the favorable acid containing 30 vol % of acetic anhydride serves as a suitable solvent. The products are 4-methyl-1, 3-dioxane, 1, 3-butanediol diacetate and 4-acetoxytetrahydropyran, and the former two of these compounds can be converted to pyran derivatives via allylcarbinol acetate. However, the formation of 4-acetoxytetrahydropyran from propylene and formaldehyde by the Prins reaction may be explained by the Baker's mechanism of hyperconjugation of the propylene methyl radical without considering the formation of allylcarbinol acetate.Various reactions of 4-hydroxytetrahydropyran are carried out and its derivatives are prepared, including several new compounds. For the sake of comparison with the reactivity of propylene, some reactions of allyl halides with formaldehyde are also studied and the main products are found to be 4-halomethyl-1, 3-dioxanes.
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