Dicyclopentadiene reactions with nitrogen oxides

The reaction is akin to the Ritter reacticm, with activation achieved by nitration, rather than protonation, and the products accordingly retain the nitro groiq). Additions to 1-phenylcyclohexene (59%) and to fra/w-stilbene (72%) are stereospecific (trans)-, cw-stilbene gives the expected threo i oduct (39%) plus some erythro (6%). Reactions of nitrogen oxide with alkenes are very complex and rarely use-ful. A recent mechanistic paper gives many key references. Addition of N2O3 is occasionally useful, as with dicyclopentadiene (Scheme 49). ... 

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