Assessing the Rates of Ring-Opening of Aziridinium and Azetidinium Ions: A Dramatic Ring Size Effect

Assessing the Rates of Ring-Opening of Aziridinium and Azetidinium Ions: A Dramatic Ring Size Effect

Rates for the ring-opening of aziridinium and azetidinium ions by DMAP were measured. The four-membered ring appears to be ca. 17 000 times less reactive compared to the three-membered ring but is still highly relevant from a synthetic viewpoint. The electrophilicity of these strained ammonium ions...

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Veröffentlicht in:Organic letters 2011-04, Vol.13 (7), p.1836-1839
Hauptverfasser: De Rycke, Nicolas, David, Olivier, Couty, François
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Organic chemistry
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Zusammenfassung:Rates for the ring-opening of aziridinium and azetidinium ions by DMAP were measured. The four-membered ring appears to be ca. 17 000 times less reactive compared to the three-membered ring but is still highly relevant from a synthetic viewpoint. The electrophilicity of these strained ammonium ions is measured for the first time.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200348k