Previous work (1,2) in this laboratory upon the pyrolysis of amylsodium has shown its instability and the influence of associated salts. In the present work this organosodium compound was pyrolyzed as a dry solid under a vacuum in order to observe if both pentane and pentene were present or (4) if the hydrocarbon were only the alkene, as had been observed in the pyrolysis of butyllithium (3). Pentane proved to be present in large amount. Pentene-1 was found at 90°a nd 75°b ut, surprisingly, irans-pentene-2 was found also, and in increasing amounts as the temperature fell. At 50°this trans isomer was the sole olefin. Pentene-1 might have changed to irans-pentene-2 if it had remained long enough -SUMMARY 1. Decomposition of amylsodium at 90, 75, and 50°under a vacuum yielded progressively less pentene-1. At the lowest temperature the olefin was entirely trans-pentene-2.2. Pentenylsodium caused the isomerization of hydrocarbons with terminal vinyl groups and the process was exceedingly rapid with any n-alkene-l tested.3. The isomerization of pentene-1 to fmns-pentene-2 took place in decreasing velocity as pentenyl-, benzyl-, octenyl-, amyl-, phenyl-, triphenylmethyl-, and allyl-(alfin) sodium compounds were used.4. With phenylsodium the isomerizing activity decreased as the sodium compound was made from chloro-, bromo-, and iodo-benzene.Cambridge 39, Mass.

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