Hydrazidohydroxylation of Styrenes with N-Acetylaminophthalimide Using Phenyliodine(III) Bis(trifluoroacetate) (PIFA)

Abstract

Regioselective hydrazidohydroxylation of styrenes with N-acetylaminophthalimide using phenyliodine(III) bis(trifluoroacetate) was carried out to afford 1-aryl-2-(N-acetyl-N-phthalimido)aminoethyl trifluoroacetates in high yields. The procedure is operationally simple and removal of trifluoroacetyl and phthalimido groups was performed by treatment of the trifluoroacetate with hydrazine hydrate in good yield. A synthetic study and a mechanistic proposal for the hydrazidohydroxylation are presented.

Key words

hydrazidohydroxylation - styrene - N-acetylamino­phthalimide - nitrenium ion - phenyliodine(III) bis(trifluoroacetate)

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11

In the intramolecular cyclization of an N-acylnitrenium ion and the olefin fragment in a molecule, Tellitu and Domínguez reported that the created carbocationic species are stabilized by the formation of aziridinium ion intermediates. See references 6j, 6l and 6m.