Abstract
An Unusual Dehydrochlorination: syn‐Elimination from a Sterically Hindered, but Free Rotating Halogenated HydrocarbonDepending on the solvent, the meso‐3, 4‐dichloro‐2,2,5,5‐tetramethylhexane undergoes base‐promoted dehydrochlorination in a syn‐ or anti‐periplanar manner, thus affording (Z)‐3‐chloro‐2,2,5,5‐tetramethyl‐3‐hexene and the thermodynamically less stable (E)‐isomer, respectively. Alcoholate aggregates of different size (presumably, dimers and trimers or tetramers) are alternatively involved in these stereochemically distinct conversions, at least when potassium t‐butoxide in t‐butyl alcohol or tetrahydrofuran serves as a base/solvent system.
Published Version
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