Journal of the Chemical Society. Perkin transactions I p. 881 - 886 (1992)
Update date:2022-07-29
Topics:
Lee, Woo Young
Sim, Wonbo
Choi, Kwang Do
Synthesis of new orthocyclophane hosts has been investigated by the acid-catalysed intramolecular Friedel-Crafts cycloalkylation of terminal benzylbenzylic alcohols that bear repeating benzyl chains.Treatment of 2-(2-benzylbenzyl)benzyl alcohol 6 with concentrated sulfuric acid in acetic acid medium gave rise to a cyclisation product, <1.1.1>orthocyclophane 2.Similar cyclisation behaviour was observed under the same reaction conditions by the use of diterminal benzylbenzylic diols, which provided a common-nuclear bisorthocyclophane.Treatment of a solution of either the α,ω-benzylic diols 1,3-bis<2-<2-(hydroxymethyl)benzyl>benzyl>benzene 16 in acetic acid or the 1,4-isomer 20 in acetic acid-dimethyl sulfoxide with concentrated sulfuric acid provided heptacyclo<19.15.0.03,19.05,10.012,17.023,28.030,35>hexatriaconta-1(21),2,5(10),6,8,12(17),13,15,19,23(28),24,26,30(35),31,33-pentadecaene 3 which is the first member of a family of novel biscyclophanes.
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