The high synthetic usefulness of aziridines has been often confined to their electrophilic nature, undergoing nucleophilic ring-opening reactions, as usually taught in organic chemistry courses. The aim of this review is to highlight other aspects of aziridine reactivity, now well out of their infancy. Indeed, aziridines can be easily metalated, generating the corresponding aziridinyl anions, which could act as nucleophiles leaving the three-membered ring functionality intact or, under certain circumstances, as carbenoids thus disclosing an interesting reactional scenery. Even if the reactivity of aziridinyl anions closely mirrors that of the corresponding oxiranyl anions, the investigations of the last 10 years demonstrated that additional factors should be taken into consideration when the generation of metalated aziridines is concern.

AZIRIDINYL ANIONS: GENERATION, REACTIVITY, AND SYNTHETIC APPLICATIONS

LUISI, Renzo
2010

Abstract

The high synthetic usefulness of aziridines has been often confined to their electrophilic nature, undergoing nucleophilic ring-opening reactions, as usually taught in organic chemistry courses. The aim of this review is to highlight other aspects of aziridine reactivity, now well out of their infancy. Indeed, aziridines can be easily metalated, generating the corresponding aziridinyl anions, which could act as nucleophiles leaving the three-membered ring functionality intact or, under certain circumstances, as carbenoids thus disclosing an interesting reactional scenery. Even if the reactivity of aziridinyl anions closely mirrors that of the corresponding oxiranyl anions, the investigations of the last 10 years demonstrated that additional factors should be taken into consideration when the generation of metalated aziridines is concern.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11586/15885
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