Intramolecular Concerted Insertion of Vinyl Cations into CH Bonds: Hydroalkylating Cyclization of Alkynes with Alkyl Chloroformates To Give Cyclopentanes

Intramolecular Concerted Insertion of Vinyl Cations into CH Bonds: Hydroalkylating Cyclization of Alkynes with Alkyl Chloroformates To Give Cyclopentanes

Tying the knot: In analogy to singlet carbenes, vinyl cations insert into CH bonds in a concerted intramolecular reaction, as shown by experimental investigations and quantum mechanical calculations. This reaction is useful for the synthesis of cyclopentane derivatives.

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Veröffentlicht in:Angewandte Chemie International Edition 2006-05, Vol.45 (19), p.3076-3079
Hauptverfasser: Biermann, Ursula, Koch, Rainer, Metzger, Jürgen O.
Format: Artikel
Sprache:eng
Schlagworte:
alkylation
alkynes
cyclopentanes
CH insertion
vinyl cations
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Beschreibung
Zusammenfassung:Tying the knot: In analogy to singlet carbenes, vinyl cations insert into CH bonds in a concerted intramolecular reaction, as shown by experimental investigations and quantum mechanical calculations. This reaction is useful for the synthesis of cyclopentane derivatives.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200504288