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Reaction of the Silver Salts of Arylnitroacetonitriles with 9‐Bromofluorene Synthesis of 9‐(α‐Cyanoarylidene)fluorenes
Author(s) -
Lianis Pygmalion S.,
Rodios Nestor A.,
Alexandrou Nicholas E.
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870371
Subject(s) - chemistry , yield (engineering) , alkylation , salt (chemistry) , silver salts , organic chemistry , medicinal chemistry , fluorenone , inorganic chemistry , catalysis , fluorene , materials science , metallurgy , polymer
The silver salts 1a–d react with 9‐bromofluorene to give both C ‐ and O ‐alkylated products 2 and 3 . The latter decompose to yield 9‐fluorenone and the α‐cyanooximes 5 . The products 2 upon treatment with NaOH/EtOH eliminate HNO 2 to afford 9‐(α‐cyanoarylidene)fluorenes 4 in 80% yield. 9‐Chloro‐9‐phenylfluorene reacts with the salt 1a to give only the C ‐alkylated product 6 in 70% yield.