22794-75-8Relevant academic research and scientific papers
A stereoselective intramolecular retro-ene reaction catalysed by aluminium chloride
Bodajla, Michal,Jones, Graeme R.,Ramsden, Christopher A.
, p. 2573 - 2576 (1997)
Reaction of 5-(2-naphthalenol)-1-pentenes with I(III) reagents results in nuclcophilic substitution at C-1 rather than [4+2] intramolecular ionic cycloaddition of the proposed intermediate arenoxenium cations. Treatment of the same precursors with aluminium chloride results in a stereoselective intramolecular cyclisation to spiroketones. Evidence that the mechanism of formation involves a cyclic aluminium intermediate is presented.
