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New Adventures in the Chemistry of Polycarboncyclic Ring Systems

I. Diels-Alder reactions of 1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4-metha- nonaphthalene (16) and 1,2,3,4,9,9-hexachloro-1,4,6,7-tetrahydro-1,4-methanonaphthalene (17) toward dienophiles N-methyl-1,2,4-triazoline-3,5-dione (MTAD), N-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and/or N-methylmaleimide (NMM) have been examined.

II. Epoxides derived from functionalized 1,4,4a,9a-tetrahydro-9,10-dioxo-1,4-methanoanthracenes (1a and 1b) undergo acid- and base-promoted intramolecular nucleophilic ring-opening to form new polycyclic alcohols.

III. The title cycloalkylidenecarbene has been generated via reaction of 8-methylenepentacyclo[5.4.0.0^{2,6}.0^{3,10}. 0^{5.9}]undecan-11-one (44) with diethyl diazomethyl-phosphonate (DAMP). This species could be trapped in situ by cyclohexene, thereby affording the corresponding cycloadduct 46a and 46b.

Identiferoai:union.ndltd.org:unt.edu/info:ark/67531/metadc278356
Date12 1900
CreatorsDong, Zhiming (Eric)
ContributorsMarchand, Alan P., Wiedenfeld, David
PublisherUniversity of North Texas
Source SetsUniversity of North Texas
LanguageEnglish
Detected LanguageEnglish
TypeThesis or Dissertation
Formatix, 102 leaves : ill., Text
RightsPublic, Copyright, Copyright is held by the author, unless otherwise noted. All rights reserved., Dong, Zhiming (Eric)

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