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A Stereoselective Intramolecular Retro-Ene Reaction Catalysed by Aluminium Chloride

โœ Scribed by Michal Bodajla; Graeme R Jones; Christopher A Ramsden*

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
609 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Reaction of 5-(2-naphthaIenol) -l-pentenes with 1(111)reagents results in nucleophilic substitutionat C-1 rather than[4+21 intramolecular ioniccycloadditionof tfreproposed intermediate arenoxenium cations. Treatment of the sameprecursors withaluminium chlorideresultsin a stereoselective intramolecular cyclisationto spiroketones. Evidencethat the mechanismof formation invotvesa cycticaluminiumintermediate is presented. @ 1997 Elsevier ScienceLtd.

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