New examples of specific base catalysis in mononuclear rearrangements of heterocycles found via a designed modification of the side chain structure

Vincenzo Frenna, Salvatore Marullo, Gabriella Macaluso, Francesca D'Anna, Domenico Spinellib, Susanna Guernelli, Camilla Zaira Lanza

Risultato della ricerca: Articlepeer review

1 Citazioni (Scopus)

Abstract

To select suitable candidates for the occurrence of specific-base-catalysis in MRH of (Z)-hydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole we have designed a modification of the side-chain structure by linking a strong electron-withdrawing system to the hydrazono group. Thus we have synthesized the (Z)-semicarbazone (3d), the (Z)-phenylsemicarbazone (3e), and the (Z)-acetylhydrazone (3f) of the above oxadiazole and examined their kinetic behavior in dioxane/water in a large range of proton concentrations (pS + 4.0 14.5). In all the pS+ range examined only a base-catalyzed process has been evidenced (no uncatalysed path occurs). The behavior at the largest pS+ values (the reactivity tends to a limiting rate constant) and that at variable concentrations of buffer have furnished clear evidence for the occurrence of a specificbase- catalysed process, thus reaching the target proposed and confirming the prevision.
Lingua originaleEnglish
pagine (da-a)125-144
Numero di pagine20
RivistaArkivoc
Volumeviii
Stato di pubblicazionePublished - 2009

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Entra nei temi di ricerca di 'New examples of specific base catalysis in mononuclear rearrangements of heterocycles found via a designed modification of the side chain structure'. Insieme formano una fingerprint unica.

Cita questo