An approach toward 1,4,7 trimethyl tetracyclo (5.3.2.0(4,9).0(8,10)); dodeca-2,5,11-triene "truncatriene".
Item
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Title
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An approach toward 1,4,7 trimethyl tetracyclo (5.3.2.0(4,9).0(8,10)); dodeca-2,5,11-triene "truncatriene".
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Identifier
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AAI9207084
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identifier
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9207084
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Creator
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Karimi, Sasan.
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Contributor
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Adviser: Klaus Grohmann
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Date
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1991
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Language
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English
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Publisher
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City University of New York.
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Subject
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Chemistry, Organic
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Abstract
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Homoaromaticity is viewed by Winstein as a cyclic "aromatic" polyene where the conjugation is broken at one or more sites by methano or ethano bridges.;Among the neutral hydrocarbons yet known (e.g. 1,4,7-cis-cis-cis cyclononatriene, triquinacene, and C{dollar}\sb{16}{dollar}-hexaquinacene), triquinacene shows a small (4.5 Kcal/mol) stabilization energy on the basis of heats of hydrogenation measurements. We are interested in the synthesis of the hydrocarbon 16, since its spherical geometry and rigidity may lead to an alignment of the p{dollar}\pi{dollar} orbital overlap in order to provide homoaromatic stabilization.;This thesis focuses on the synthesis of the key intermediate 12, an intramolecular alkylation (54 to 57 and 92 to 93) to construct a tricyclic carbon skeleton, and formation of the tetracyclo- (4.4.0.0{dollar}\sp{lcub}1,6{rcub}{dollar}.0{dollar}\sp{lcub}2,4{rcub}{dollar}) -decane-5-one framework (54 to 58 and 55 to 72) via possible Favorskii or S{dollar}\sb{lcub}\rm N{rcub}{dollar}2{dollar}\sp\prime{dollar} rearrangements.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI).
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Type
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dissertation
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Source
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PQT Legacy CUNY.xlsx
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degree
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Ph.D.
