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RESEARCH PRODUCT

Mononuclear heterocyclic rearrangements—vi

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Publisher Summary This chapter discusses the mononuclear heterocyclic rearrangements. The chapter discusses the ring conversion of type 1→2 characterized by nucleophilic attack from a Z atom on a sp 2 -nitrogen atom with displacement of an atom. On this basis, the known ring conversions are tabulated. Taking into account the reactivities observed in the rearrangements, results are presented for 1,2,4-oxadiazole, isoxazole, and 1,2,5-oxadiazole. The sequence involving an oxime group in the side chain is discussed. The chapter presents several attempts for inducing rearrangements in which the reaction center of the starting ring is an atom other than nitrogen. Rearrangement of arylhydrazones ( Z -isomers) of 3-benzoyl-5-phenyl-1,2,4-oxadiazole in dioxane/water, and rearrangement and isomerization of phenylhydrazone ( E - and Z -isomers) of 3-benzoyl-5-phenyl-1,2,4-oxadiazole in benzene are discussed.