Formation of Cyclic Allenes and Cumulenes by Cooperative Addition of Frustrated Lewis Pairs to Conjugated Enynes and Diynes

Formation of Cyclic Allenes and Cumulenes by Cooperative Addition of Frustrated Lewis Pairs to Conjugated Enynes and Diynes

Eight, not six: The intramolecular frustrated Lewis pair 1 reacts with conjugated enynes and diynes by 1,4‐addition to yield the corresponding eight‐membered cyclic allenes 2 and cumulenes 3, respectively. The thermodynamically more favorable 1,2‐addition (formation of six‐membered‐ring products) is...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-03, Vol.49 (13), p.2414-2417
Hauptverfasser: Mömming, Cornelia M, Kehr, Gerald, Wibbeling, Birgit, Fröhlich, Roland, Schirmer, Birgitta, Grimme, Stefan, Erker, Gerhard
Format: Artikel
Sprache:eng
Schlagworte:
boron
cyclic allenes
cyclic cumulenes
frustrated Lewis pairs
phosphorus
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Zusammenfassung:Eight, not six: The intramolecular frustrated Lewis pair 1 reacts with conjugated enynes and diynes by 1,4‐addition to yield the corresponding eight‐membered cyclic allenes 2 and cumulenes 3, respectively. The thermodynamically more favorable 1,2‐addition (formation of six‐membered‐ring products) is not observed, which indicates that the observed addition is a kinetically controlled reaction.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200906697