Diels–Alder trapping of an o-dinitroso intermediate in the 1-oxide/3-oxide interconversion of a 2,1,3-benzoxadiazole derivative

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Muriel Sebban, Régis Goumont, Jean Claude Hallé, François Terrier and Jérome Marrot


Abstract

Convincing evidence is presented that the o-dinitroso intermediate involved in the exchange of the 1-oxide and 3-oxide tautomers of 6-nitro[2,1,3]oxadiazolo[4,5-b]pyridine 1-oxide 5 is the precursor of the Diels–Alder diadduct 7 isolated upon treatment of this compound with cyclohexadiene in CHCl3.


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