Has anybody synthesized di- or higher nitrated cyclopentadienes possibly with methyl or other groups in the 1 position (analogs of TNT)?


Mono-nitrated cyclopentadienes and their benzo-analogues (indene, fluorene) have been prepared in the context of studies on nitro-aci-tautomerism.

As far as higher substitution is concerned, there seems to be at least a crystal structure of potassium dinitrotrichlorocyclopentadienide reported in Acta Cryst., B

In the abstract, the authors (Y. Otaka, F. Marumo, and Y. Saito) mention the preparation of this compound by Haga in 1969, (sorry, reference is behind paywall) via

nitration of hexachlorocyclopentadiene with alkali nitrite in an aqueous or ethanolic solution

NOTE: Hexachlorocyclopentadiene once was a favoured starting material in the synthesis of insecticides via Diels-Alder reaction. However, it is a potent teratogen and the "mother" of least five members of the dirty dozen (persistent organic pollutants) nowadays banned for good reason.

You might want to read the MSDS and then decide that you'd rather prefer to work with something else.

  • $\begingroup$ Thank you K.W. for the references. No need by me for MSDS ;-) - not in the biz -- just a curiosity of mine in analogy to TNT! I am sure that even if the more highly substituted CPD compounds could be made they would be horrendously explosive; maybe as stable as nitroglycerine itself! Thanks again! No reply needed. $\endgroup$ – Jeffery C. Niemuth Apr 20 '14 at 20:46

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