ChemInform Abstract: Isocamphanone and Its Oxime in the Croton Cross Condensation with Acetone. Reaction of the Obtained α,β-Unsaturated Compounds under Ritter Reaction Conditions.
✍ Scribed by S. S. Koval'skaya; N. G. Kozlov
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 33 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Isocamphanone and Its Oxime in the Croton Cross Condensation with Acetone.
Reaction of the Obtained α,β-Unsaturated Compounds under Ritter Reaction Conditions.
-Base-catalyzed croton condensation of isocamphanone (I) with acetone affords a mixture of E-(III) and Z-oxopropylidene derivatives (IV), i.e. isocamphanone acts exclusively as carbonyl component. An attempt to obtain the alternative condensation product (isocamphanone acting as methylene component) by masking the ketone as ketal is not successful. In contrast, the E-oxime (VII) readily reacts as methylene component with acetone to furnish the isopropylideneisocamphanone (VIII). The condensation products (III)/(IV) and (VIII) undergo a skeletal rearrangement under Ritter reaction conditions to furnish bicyclo[4.2.1]nonane derivative (VI) or 3-azabicyclo[3.2.1]octene derivative (IX), respectively. -