Beiträge zur Stereochemie der Additionsreaktionen an 3,4,5,6-Tetrahydropyridin-1-oxide. 2. Mitt.

4-tert-Butyl-3,4,5,6-tetrahydropyridine-1-oxide (1) and 6-butyl-3,4,5,6-tetrahydropyridine-1-oxide (2) were prepared and isolated in their monomeric forms. In many aprotic solvents these compounds are converted into their dimers. The main product in both cases is the addition product of identical enantiomers. In the case of compound1 a very small amount of an addition product of the optical antipodes is also formed, which is the thermodynamically most stable isomer. In contrast, compound2 yielded an addition product of the optical antipodes in larger amounts, with a thermodynamically less favourable structure. These dimerizations are solvent dependent, reversible and sensitive to steric hindrance.