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Reduction of Phenyl Silyl Acetylenes with Lithium: Unexpected Formation of a Dilithium Dibenzopentalenide
Author(s) -
Saito Masaichi,
Nakamura Michio,
Tajima Tomoyuki,
Yoshioka Michikazu
Publication year - 2007
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.200604067
Subject(s) - dilithium , silylation , lithium (medication) , chemistry , psychology , organic chemistry , psychiatry , ion , catalysis , deprotonation
The degree of bulkiness of the silyl substituent strongly affects the reduction mode of phenyl silyl acetylenes. For example, the treatment of phenyl(triisopropylsilyl)acetylene with lithium led to the unprecedented formation of a dilithium dibenzopentalenide together with the expected 1,4‐dilithio‐1,3‐butadiene (see scheme), whereas the reduction of phenyl( tert ‐butyldimethylsilyl)acetylene gave only the corresponding 1,4‐dilithio‐1,3‐butadiene.