Diverse modes of reactivity of 6-(chloromethyl)-6-methylfulvene

European J Org Chem. 2017 May 26;2017(20):2925-2931. doi: 10.1002/ejoc.201700442.

Abstract

The title compound exhibits a number of reactivities toward nucleophiles/bases owing to the presence of several electrophilic and potentially nucleophilic sites in the molecule. We explored the reactions of 6-(chloromethyl)-6-methylfulvene with oxygen- and nitrogen nucleophiles and bases as well as a carbon-based nucleophile (an enamine) and realized all possible reactivity modes predicted on the basis of electrophilic and nucleophilic positions in this compound.

Keywords: 1,2-Dihydropentalene; Dipolar cycloaddition; E1cB; Fulvenes; Nucleophilic addition.