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Studies of BN-Isosteres of Carbocyclic Systems

Thesis advisor: Shih-Yuan Liu / The first three chapters of this dissertation elaborate on certain facets of the isosteric relationship between different types of boron-nitrogen-containing heterocycles and the corresponding all-carbon compounds. In this vein, Chapter 1 describes selective photoisomerization of aromatic 1,2-dihydro-1,2-azaborines to BN-analogues of bicyclo[2.2.0]hexa-2,5-diene (Dewar benzene). In one instance, the photoisomer product was further derivatized into a series of disubstituted cyclobutanes through manipulations of the boron functionality. Chapter 2 discloses a combined experimental/theoretical mechanistic investigation of preliminary hydrogen release from the amine borane unit in a pair of BN-cycloalkanes. In Chapter 3, the kinetics of complementary dehydrogenation of the alkyl units in a BN-cyclohexene derivative are compared with those of related six-membered carbocycles. Chapter 4 treats with the separate subject of enantioselective silylation of glycerol by a catalytic strategy centered around reversible covalent binding of substrate hydroxyl groups. / Thesis (PhD) — Boston College, 2018. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.

Identiferoai:union.ndltd.org:BOSTON/oai:dlib.bc.edu:bc-ir_108092
Date January 2018
CreatorsGiustra, Zachary Xavier
PublisherBoston College
Source SetsBoston College
LanguageEnglish
Detected LanguageEnglish
TypeText, thesis
Formatelectronic, application/pdf
RightsCopyright is held by the author, with all rights reserved, unless otherwise noted.

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