Synthesis and aldol cyclotrimerization of 4, 7-di-tert-butylacenaphthenone

AW Amick, KS Griswold…

Index: Amick, Aaron W.; Griswold, Keith S.; Scott, Lawrence T. Canadian Journal of Chemistry, 2006 , vol. 84, # 10 p. 1268 - 1272

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Citation Number: 7

Abstract

An efficient gram scale synthesis of the previously unknown 4, 7-di-tert- butylacenaphthenone (3b) is reported. The facile isomerization of epoxide 9b to ketone 3b occurs simply on stirring a solution of 9b with silica gel at room temperature. Aldol cyclotrimerization of 3b with titanium tetrachloride gives 2, 5, 8, 11, 14, 17-hexa-tert-butylde cacyclene (1b) in 58% isolated yield. X-ray crystal structures have been obtained for the ...