Tetracyanazulene has many potential uses including molecular magnets.   This work will focus on 2,4,6,8-tetracyanoazulene (TCNA).  It can be synthesized from 2-cyanoazulene by sequential cyanide addition followed by oxidation (re-aromatization) using chloranil.  The challenge in preparation of TCNA is synthesis of the precursor 2-cyanoazulene.  Two literature preparations are known, but they involve 6-7 steps within several low yielding steps and difficult purifications.  We will present an alternative one-pot synthesis based on the synthesis of 6-cyanoazulene from cyanopyridine via its Zincke salt. Preliminary B3LYP/6-31G* LUMO calculations on 6-cyanoazulene indicate that the cyano group should direct subsequent �CN nucleophiles to the desired 2, 4, and 8 positions.

Designing a new synthesis of 2,4,6,8-tetracyanoazulene for use in molecular magnets

247th National Meeting (2014)

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