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Azulene functionalization by iron-mediated addition to a cyclohexadiene scaffold
OAI: oai:purehost.bath.ac.uk:openaire_cris_publications/01ffb143-0ebe-4152-9072-20f8fe6c9629 • DOI: https://doi.org/10.1021/acs.joc.0c01412
Abstract
The functionalization of azulenes via reaction with cationic η5-iron carbonyl diene complexes under mild reaction conditions is demonstrated. A range of azulenes, including derivatives of naturally occurring guaiazulene, were investigated in reactions with three electrophilic iron complexes of varying electronic properties, affording the desired coupling products in 43−98% yield. The products were examined with UV− vis/fluorescence spectroscopy and showed interesting halochromic properties. Decomplexation and further derivatization of the products provide access to several different classes of 1-substituted azulenes, including a conjugated ketone and a fused tetracycle.