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Chemistry of adamantanes and related compounds. Diazotization of endo-7-aminomethylbicyclo[3.3.1]nonan-3-one and endo-3-aminomethylbicyclo[3.3.1]nonane

✍ Scribed by Liu, Jih-Hua; Kovacic, Peter

Book ID: 121322118
Publisher: American Chemical Society
Year: 1973
Tongue: English
Weight: 683 KB
Volume: 38
Category: Article
ISSN: 0022-3263
DOI: 10.1021/jo00960a004

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We have recently described' rapid reversible 3,7-hydride transfer in the alkoxide of exo-bicyclo[3.3.11 nonan-7-ol-3-one (1). We now report the base-induced rearrangement of the title compound (3) to anti-7,7-dimethylbicycl0[3.3.l]nonan-9-ol-3-one (4) , a process involving 3,9-hydride transfer withi