The nature and stereoisomeric distribution of neutral products obtained from the gas-phase attack of radiolytically formed Broensted and Lewis acids on substituted 1,2-epoxycyclohexanes were studied under different exptl. conditions. Highly regio- and stereoselective cationic nucleophilic displacements, with complete inversion of configuration at the reaction center, were obsd. In some cases, extensive acid-induced isomerization became the only observable pathway. The relative extent of competing substitution and isomerization depend on several factors, including the structure features and internal-energy excess of the oxonium derivs. of the epoxy substrates.

GAS-PHASE ACID-INDUCED RING-OPENING IN SUBSTITUTED 1,2-EPOXYCYCLOHEXANES / P., Crotti; F., Macchia; A., Pizzabiocca; G., Renzi; Speranza, Maurizio. - In: GAZZETTA CHIMICA ITALIANA. - ISSN 0016-5603. - STAMPA. - 117:(1987), pp. 739-745.

GAS-PHASE ACID-INDUCED RING-OPENING IN SUBSTITUTED 1,2-EPOXYCYCLOHEXANES

SPERANZA, Maurizio
1987

Abstract

The nature and stereoisomeric distribution of neutral products obtained from the gas-phase attack of radiolytically formed Broensted and Lewis acids on substituted 1,2-epoxycyclohexanes were studied under different exptl. conditions. Highly regio- and stereoselective cationic nucleophilic displacements, with complete inversion of configuration at the reaction center, were obsd. In some cases, extensive acid-induced isomerization became the only observable pathway. The relative extent of competing substitution and isomerization depend on several factors, including the structure features and internal-energy excess of the oxonium derivs. of the epoxy substrates.
1987
01 Pubblicazione su rivista::01a Articolo in rivista
GAS-PHASE ACID-INDUCED RING-OPENING IN SUBSTITUTED 1,2-EPOXYCYCLOHEXANES / P., Crotti; F., Macchia; A., Pizzabiocca; G., Renzi; Speranza, Maurizio. - In: GAZZETTA CHIMICA ITALIANA. - ISSN 0016-5603. - STAMPA. - 117:(1987), pp. 739-745.
File allegati a questo prodotto
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/460730
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? 8
social impact