Tetrahedron Letters p. 1501 - 1504 (1981)
Update date:2022-08-17
Topics:
Farcasiu, Malvina
Hagaman, Edward W.
Wenkert, Ernest
Schleyer, Paul von Rague
Unexpected differences in the aluminium bromide-catalyzed rearrangement behavior of 1,2-endo-trimethylenenorbornane (1) and its 1,2-exo-isomer (2) are interpreted.Isotopic labelling studies indicate that reversible abstraction of the tertiary 2-endo hydride in 2 does not occur (Scheme 1).Instead, rearrangement to 6 is favored.The label scrambling in the final product, adamantane (8), is attributed to degenerate isomerization in the protoadamantyl precursor, 7.
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