CH3CH(O14CH2CH3)2 and CH2CHO14CH2CH3 have been synthesized from CH3CHO and CH314CH2OH. The synthesized vinyl ethyl ether (b.p. 35.5°) is accompanied by diethyl ether (b.p. 34.6°) and other impurities. A satisfactory separation has been made by gas chromatography in a 2 m dimethylsulfolane column followed by a 3 m squalane column on Celite. In this way, 0.5 ml of CH314CH2OCHCH2 of 99.4% chemical purity and 98.3% radiochemical purity has been obtained; the position of the C-14 has been checked by hydrolysis in acid medium. The ether was pyrolyzed in a high vacuum apparatus by the static method. The amounts and specific activities of products were determined in a gas chromatograph connected to a flow ionization chamber with vibrating reed electrometer. Results obtained around 450°C seem to prove that vinyl ethyl ether decomposes mainly (78%) by a rearrangement process forming an hexagonal activated complex.
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Molera et al. (1968) studied this question.