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Synthesis and Characterization of Organosilicon Substituted Fluorenyl Derivatives
Author(s) -
Khan Shah Alam
Publication year - 2004
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200400184
Subject(s) - chemistry , fluorene , organosilicon , anhydrous , yield (engineering) , chloride , organic chemistry , halogenation , nucleophilic substitution , medicinal chemistry , magnesium , friedel–crafts reaction , catalysis , materials science , metallurgy , polymer
Abstract Friedel‐Crafts cycloalkylation of biphenyl with 2,3‐dichlorobutyltrichlorosilane(Cl 3 Si‐CH 2 CHClCHClCH 3 ) at a temperature of 100°C in the presence of anhydrous aluminum chloride catalyst gave cyclized product, 9‐methyl‐9‐(2‐trichlorosilylethyl)fluorene 1a , in 33% yield. Methylation of 1a with nucleophilic reagent such as methyl magnesium chloride, gave 9‐methyl‐9‐(2‐trimethylsilylethyl)fluorene 2 while bromination of 2 with excess amount of bromine in DMF resulted in 2,7‐dibromo‐9‐methyl‐9‐(2‐trichlorosilyl)fluorene 3 in good yield. All the compounds were structurally identified by GC/MS, 1 H and 13 C‐NMR spectroscopy.