Heterocyclic Spirocyclohexadienones, IThe compound formerly described as methylene amine 3 is in fact the heterocyclic spirocyclohexadienone 9. Contrary to literature, catalytic hydrogenation does not lead to methylamine 4 but to spiroketone 10 and a mixture of diastereomeric spirocyclic alcohols l l d l l b . The reactivity of 9 with protonic acids and carbonyl reagents is investigated.
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Heterocyclic Spirocyclohexadienones. Part 1.-The dinaphthylmethane derivative (I) (synthesis given) reacts with paraformaldehyde (II) to yield the spiro-fused cyclohexadienone (III) via intramolecular ipsoaminoalkylation. Hydrogenation of (III) leads to the formation of the spiroketone (IV) and the diastereoisomeric spirocyclic alcohols (V). The perchlorate of (III), (VI), reacts with the alcohols (VII) to give the ethers (VIII). No oximation takes place with hydroxylamine hydrochloride: a mixture of the acridine derivatives (IX) and (X) is formed instead. -(MOEHRLE, H.; SCHAKE, D.; BLUHME-HENSEN, K.; Arch.
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