Approaches to the synthesis of triterpenoids: V: an unusual acid-catalysed rearrangement of a beta-gamma unsaturated ketone

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TypeArticle
Journal titleCanadian Journal of Chemistry
Volume56
Pages21502155; # of pages: 6
AbstractThe reaction of 2-keto-lIJ,4a(3-dimethyl-la-[2-(3-keto-1,4,4-trimethylcyclohexyl)ethyl]-7- methoxy-l,2,3,4,4a,9-hexahydrophenanthrenlea and b with p-toluenesulphonic acid in boiling xylene yields the rearranged product, 1 ,lo-dimethyl-2-[2-(3-keto-I ,4,4-trimethy1cyclohexyl)- ethyl]-7-methoxy-3,4-dihydroanthracene (3). Crystals of 3 are monoclinic, space group P2,/c, Z = 4, with a = 7.2684(3), b = 30.942(2), c = 10.5544(7) A, (3 = 98.24(1)". The structure was determined by direct methods from diffractometer data and refined by blockdiagonal least-squares to an R of 0.043 for 1810 observed reflections. The molecule exhibits no unusual geometric features, although positional disorder is apparent in the cyclohexanone moiety.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Institute for Chemical Process and Environmental Technology; NRC Steacie Institute for Molecular Sciences
Peer reviewedYes
NRC number16724
NPARC number16296147
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Record identifierb25548e2-2ab6-4b94-8142-d98660c6fa0e
Record created2010-11-04
Record modified2016-05-09
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