Journal of the Chemical Society. Perkin transactions I p. 565 - 573 (1981)
Update date:2022-09-26
Topics: Intramolecular Cycloaddition
Bishop, Roger
Parker, William
Stevenson, James Ronald
Reactions likely to involve C(2)-C(6) and C(2)-C(7) intramolecular reactions in bicyclo<3.3.1>nonane derivatives are discussed in terms of the conformations available to the ring system.While endo-6-hydroxybicyclo<3.3.1>nonan-2-one (11) incorporated three deuterium atoms (excluding the hydroxy-group) on heating with NaOD, the exo-isomer (17) exchanged the six hydrogens adjacent to the oxygenation functions but not the carbinyl proton.Evidence is presented favouring a stereospecific base-induced 2,6-hydride migration, most probably proceeding via a twin-twist boat transition state.Treatment of 6,6-ethylenedioxy-2-methoxymethylenebicyclo<3.3.1>nonane (36) with aqueous HCl in acetone produced 2-hydroxyprotoadamantan-10-one (38) in high yield.This process resulted from hydrolysis of the oxygenated groups thereby liberating the endo-keto-aldehyde intermediate (37) which underwent subsequent intramolecular aldol condensation between the C(2) aldehyde and C(7).
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