Reactions of Alkenyl Fischer Carbene Complexes with Ketene Acetals: Formation of Alkynes

Reactions of Alkenyl Fischer Carbene Complexes with Ketene Acetals: Formation of Alkynes

Alkenyl Fischer carbene complexes with an isopropoxy group on the carbene carbon will react with ketene acetals by 1,4‐addition to give a zwitterionic intermediate, which undergoes subsequent internal isopropoxide transfer to generate a vinylidene complex. Either a hydrogen or phenyl group on the vi...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:European Journal of Organic Chemistry 2006-12, Vol.2006 (23), p.5219-5224
Hauptverfasser: Wang, Siu Ling B., Liu, Xuejun, Ruiz, Miriam C., Gopalsamuthiram, Vijay, Wulff, William D.
Format: Artikel
Sprache:eng
Schlagworte:
Fischer carbene complex
Ketene acetal
Michael addition
Rearrangement
Vinylidene complex
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Alkenyl Fischer carbene complexes with an isopropoxy group on the carbene carbon will react with ketene acetals by 1,4‐addition to give a zwitterionic intermediate, which undergoes subsequent internal isopropoxide transfer to generate a vinylidene complex. Either a hydrogen or phenyl group on the vinylidene carbon will undergo a formal 1,2‐migration to give 4‐pentynoate esters after hydrolysis of the intermediate orthoester. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200600672