Nucleophilic elimination, substitution, addition, and cyclisation reactions of polychlorocyclopentadiene dimers

Abstract

Dehydrohalogenation and subsequent nucleophilic substitution–addition reactons of pentachlorocyclopentadiene dimer are described. Mechanistic pathways (including the possibility of 2p–4π interaction leading to a stabilised intermediate carbanion) to account for the ready formation of (largely) a single triether when the dimer is treated with potassium methoxide, are briefly discussed. Intramolecular cyclisation and rearrangements of derivatives of the triether (and related compounds) are described.