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An interesting substituent effect on the acid-catalyzed skeletal rearrangement of seco-homocubanes

โœ Scribed by J. M. J. Vankan; A. J. H. Klunder; J. H. Noordik; B. Zwanenburg

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
221 KB
Volume
99
Category
Article
ISSN
0165-0513

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โœฆ Synopsis

Abstract

The acid catalyzed rearrangement of 1โ€bromotetracyclo[4.3.0.0^2.5^0^3.8^]nonanโ€4โ€one 1b has been studied. With aqueous HBr, the exclusive formation of 2,7โ€dibromotricyclo[4.2.1.0^3.7^]โ€nonanโ€4โ€one 4b was observed. This structure was established by Xโ€ray analysis. The divergency in behaviour of secoโ€homocubane 1b and its 9โ€ethylene acetal derivative 1a towards acidic reagents reveals a directing effect of the 9โ€ethylene acetal function on the skeletal rearrangement.

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