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Synthesis and reactions of a novel bulky aryllithium
Author(s) -
Saito Masaichi,
Okuyama Yuta,
Tajima Tomoyuki,
Kato Daichi,
Yoshioka Michikazu
Publication year - 2007
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1268
Subject(s) - chemistry , phenyllithium , electrophile , fluorene , carbon tetrachloride , benzyl chloride , trimethylsilyl , chloride , tetrachloride , organic chemistry , medicinal chemistry , friedel–crafts reaction , trimethylsilyl chloride , polymer chemistry , catalysis , tin , polymer
A novel bulky aryllithium, 2,6‐bis{2,5‐bis[bis(trimethylsilyl)methyl]phenyl}phenyllithium (BbspLi), was synthesized. Reactions of BbspLi 5 with Group 14 electrophiles, such as stannous chloride, with carbon tetrachloride or tetrachlorometallanes gave fluorene 6 . Reaction of BbspLi with carbon tetrachloride gave benzyl chloride 8 , which converted to 6 under acidic conditions. BbspLi 5 isomerized to the corresponding benzyl anion 10 , which underwent halophilic reactions with Group 14 electrophiles to give fluorene 6 via the benzyl chloride intermediate 8 . Copyright © 2007 John Wiley & Sons, Ltd.
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