TY - JOUR
T1 - Reduction of phenyl silyl acetylenes with lithium
T2 - Unexpected formation of a dilithium dibenzopentalenide
AU - Saito, Masaichi
AU - Nakamura, Michio
AU - Tajima, Tomoyuki
AU - Yoshioka, Michikazu
PY - 2007/6/27
Y1 - 2007/6/27
N2 - (Chemical Equation Presented) 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.
AB - (Chemical Equation Presented) 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.
KW - Alkynes
KW - Aromatic systems
KW - Intermolecular cyclization
KW - Metalation
KW - Reduction
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U2 - 10.1002/anie.200604067
DO - 10.1002/anie.200604067
M3 - Article
C2 - 17387657
AN - SCOPUS:34250711880
SN - 1433-7851
VL - 46
SP - 1504
EP - 1507
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 9
ER -