Solvolysis reactions at the 13th carbon of 1-aryl organoiron complexes

Acid-catalysed solvolysis procedures exchange protecting groups on benzyl alcohol derivatives in the synthesis of eta(5) 1-arylcyclohexadienyliron building blocks for alkaloid synthesis. The reaction proceeds via a carbocation intermediate which can also be intercepted by intramolecular electrophilic addition to the tricarbonyl(eta(4)-diene)iron(0) moiety to provide a novel and high-yielding cyclisation reaction forming a 5a alpha-cyanomethyl-5a,8a-dihydrofluorene tricarbonyliron complex in 96% yield. (C) 2009 Elsevier Ltd. All rights reserved