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Formation of Cyclic Allenes and Cumulenes by Cooperative Addition of Frustrated Lewis Pairs to Conjugated Enynes and Diynes
Author(s) -
Mömming Cornelia M.,
Kehr Gerald,
Wibbeling Birgit,
Fröhlich Roland,
Schirmer Birgitta,
Grimme Stefan,
Erker Gerhard
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200906697
Subject(s) - frustrated lewis pair , intramolecular force , conjugated system , chemistry , ring (chemistry) , lewis acids and bases , yield (engineering) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , polymer , metallurgy
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.