Are highly nitrated cyclopentadiene compounds possible?

Are highly nitrated cyclopentadiene compounds possible?


1 Answers

askIITians Faculty 747 Points
7 years ago
Mono-nitrated cyclopentadienes and their benzo-analogues (indene, fluorene) have been prepared in the context of studies onnitro-aci-tautomerism.

As far as higher substitution is concerned, there seems to be at least a crystal structure ofpotassium dinitrotrichlorocyclopentadienidereported inActa Cryst., B

In the abstract, the authors (Y. Otaka, F. Marumo, and Y. Saito) mention the preparation of this compound byHagain 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 apotent teratogenand the "mother" of least five members of thedirty dozen(persistent organic pollutants) nowadays banned for good reason.

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