Medium-size cyclophanes. Part 601: Synthesis and conformational studies of 9-substituted [3.3] metacyclophane-2, 11-diones and conversion to the corresponding [ …

T Yamato, K Tsuchihashi, N Nakamura…

Index: Yamato, Takehiko; Tsuchihashi, Koji; Nakamura, Noriko; Hirahara, Mai; Tanaka, Kan Canadian Journal of Chemistry, 2002 , vol. 80, # 5 p. 510 - 516

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Citation Number: 8

Abstract

Various syn-and anti-9-substituted [3.3] metacyclophane-2, 11-diones are obtained by the coupling reaction of the corresponding 2, 6-bis (bromomethyl) benzenes (3) with 2, 6-bis [2- cyano-2-(toluenesulfony) ethyl]-4-tert-butyl-1-substituted benzenes (4) in dimethylformamide (DMF) with an excess of sodium hydride. Depending on the substituents at positions 1 and 4 on 3, different yields (inversion of selectivity) of anti-5 and syn-5 were achieved. Key ...