TITLE

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

AUTHOR(S)
Amick, Aaron W.; Griswold, Keith S.; Scott, Lawrence T.
PUB. DATE
October 2006
SOURCE
Canadian Journal of Chemistry;Oct2006, Vol. 84 Issue 10, p1268
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
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 synthetic intermediates 4,7-di-tert-butylacenaphthene (2b) and 4,7-di-tert-butylacenaphthylene (8b).
ACCESSION #
24715605

 

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