The preparation and properties of small ring fused benzenes and naphthalenes

dc.contributor.advisorThummel, Randolph Paul
dc.contributor.committeeMemberGeanangel, Russell A.
dc.contributor.committeeMemberKohn, Harold Lewis
dc.contributor.committeeMemberWelch, Steven C.
dc.contributor.committeeMemberKimball, Aubrey P.
dc.creatorNutakul, Wutichai
dc.description.abstractBenzocyclobutene may be prepared by a three-step route first involving the Diels-Alder addition of butadiene to dimethylCyolobutene- 1,2-dicarboxylate. The resulting diester adduct may be hydrolyzed to the corresponding dicarboxylic acid which upon treatment with two equivalents of lead tetraacetate undergoes bis-decarboxylation and aromatization of the six-membered ring. By substituting different dienes into this scheme, a series of bis-annelated benzene isomers in which the benzene portion was fused to a four-, five- or six-membered ring has been prepared. When 1,1-dicyclobutenyl is used in this scheme, tricyclobutabenzene was obtained. The Diels-Alder addition of 1,2-dimethylenecyclobutane to dimethyl- cyclobutene-1,2-dicarboxylate provides the tricyclic diester 159. Pyrolysis promotes cyclobutene ring opening to diene 160 which can then be added to a second equivalent of dienophile to give the tetracyclic tetraester 161. Hydrolysis to tetraacid followed by oxidative decarboxylation and aromatization gives naphtho[b,e]dicyclobutene. [...]
dc.description.departmentChemistry, Department of
dc.format.digitalOriginreformatted digital
dc.rightsThis item is protected by copyright but is made available here under a claim of fair use (17 U.S.C. Section 107) for non-profit research and educational purposes. Users of this work assume the responsibility for determining copyright status prior to reusing, publishing, or reproducing this item for purposes other than what is allowed by fair use or other copyright exemptions. Any reuse of this item in excess of fair use or other copyright exemptions requires express permission of the copyright holder.
dc.titleThe preparation and properties of small ring fused benzenes and naphthalenes
dc.type.genreThesis of Natural Sciences and Mathematics, Department of of Houston


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