Journal of the Chemical Society. Chemical communications p. 1558 - 1560 (1986)
Update date:2022-08-11
Topics:
Rautenstrauch, Valentin
Reduction of five bicyclo<2.2.1>heptan-2-ones (6), (9), (12), (15), (18) and the parent bicyclo<2.2.1.>hept-5-en-2-one (21) by alkali metals dissolving in NH3 and a cosolvent saturated with NH4Cl affords in every case predominantly (83 -> 99percent) the corresponding endo-alcohol (7), (10), (13), (16), (19), and (22), and since two of these endo-alcohols are the thermodynamically more stable <(7), (19)> and two the less stable <(10), (13)> isomers, these reductions are probably all kinetically controlled; a correlation is made between this endo-selectivity and exo-hydrogen-exchange in the ketones (6), (9), (12), (15), and (21).
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