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Regiospecific ring enlargement of 2-noradamantanone 4- or to 5-protoadamantanone. Application to the synthesis of adamantane-1-13C.

✍ Scribed by Malvina Fǎrcaşiu; Dan Fǎrcaşiu; Joel Slutsky; Paul von Ragué Schleyer

Book ID: 104243203
Publisher: Elsevier Science
Year: 1974
Tongue: French
Weight: 217 KB
Volume: 15
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)92083-0

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✦ Synopsis

We have developed an efficient synthesis of bridgehead carbon-labelled adamantane starting 2-noradamantanone (I).' Two of the three steps involved are mechanistically revealing.

Tb.e preferential attack of I by nucleophiles from the equatorial direction (exe side) is established.' We have utilized this stereoselectivity to achieve regioselective ring

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