On the Thermal Isomerization of trans-Cyclooctene to cis-Cyclooctene

Article abstract of DOI:10.1021/jo00341a021

The thermal isomerization of trans-1,2-dideuteriocyclooctene in adequately conditioned Pyrex ampules gives cis-1,2-dideuteriocyclooctene, a result which excludes radical chain, <1,3> hydrogen shift, and <1,2> hydrogen shift mechanisms.When inadequately conditioned ampules are employed, deuterium scrambling is evident in the cis-cyclooctene formed but not in the trans-cyclooctene recovered.