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The synthesis and x-ray crystal structure of a tetracyclo[4.2.1.1.2,503,7]decane derivative. A rigid, twist boat-containing ring system.

✍ Scribed by David J. Herbert; John R. Scheffer; Anthony S. Secco; James Trotter

Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 213 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)81794-9

No coin nor oath required. For personal study only.

✦ Synopsis

Attempted intramolecular pinacolization of cage diketone 4 unexpectedly gave ketol 5 instead. %

Compound 5 was shown to possess the rare tetracyclo[4.2.?.1.2,503~7]decane ring system by means of an X-ray crystal structure of hydroxy-mesylate J&j derived from 2 by sodium borohydride reduction followed hy mesylation.

A possible mechanism for the transformation of $,f~:;,~,f.s presented, and certain noteworthy features of the crystal structure of &Q are

The base-catalyzed fragmentation of 2 to give enone J.J is also described.

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