The regiochem. outcome of the ring-opening of epoxides bearing remote polar functionalities was established in the case of carbocyclic and furanosidic epoxides I (X = O, CH2).  Under std. conditions, the regioisomeric C(1) products are the sole (from trans epoxides) or predominant (from cis epoxides) ring-opening products.  However, under chelating conditions, and only in the case of the cis epoxides, a consistent increase in C(2) selectivity is unexpectedly obsd.

Regiochemical Control of the Ring Opening of Epoxides by Means of Chelating Processes. 13. Synthesis and Ring-Opening Reactions of the Distereoisomeric cis- and trans Epoxides Derived from 3-(Benzyloxy)cyclopentene and 2-(Benzyloxy)-2,5-dihydrofuran

CROTTI, PAOLO;DI BUSSOLO, VALERIA;FAVERO, LUCILLA;PINESCHI, MAURO
1998

Abstract

The regiochem. outcome of the ring-opening of epoxides bearing remote polar functionalities was established in the case of carbocyclic and furanosidic epoxides I (X = O, CH2).  Under std. conditions, the regioisomeric C(1) products are the sole (from trans epoxides) or predominant (from cis epoxides) ring-opening products.  However, under chelating conditions, and only in the case of the cis epoxides, a consistent increase in C(2) selectivity is unexpectedly obsd.
Crotti, Paolo; DI BUSSOLO, Valeria; Favero, Lucilla; F., Macchia; Pineschi, Mauro
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/205160
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