高原子価ヨウ素化合物によるN-Acylaminophthalimide類とオレフィン類とのHydrazidohydroxylation反応について

抄録

Divalent positively charged nitrogen species (nitrenium ions) which are stabilized by the neighboring groups have been greatly applied in the field of synthetic organic chemistry. Previously, we reported that nitrenium ions (I) can be generated from the corresponding N-methoxy- or N-allyloxy-N-chloroamides by the action of silver or zinc ions or by direct oxidation of the corresponding amides with phenyliodine(III) bis(trifluoroacetate) (PIFA). Later, we also reported that nitrenium ions (II), generated from N-acylaminophthalimide with PIFA, react with arenes to give nitrogen heterocycles. In an extension of this work, we have investigated the reaction of II with olefins to give hydrazide derivatives having a trifluoroacetoxy group on the adjacent carbon in good yields. The procedure is operationally simple and the reaction is extremely regioselective.

Scheme 1