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Title: The chemistry of bifunctional molecules containing the dimesitylboron group
Author: Mittoo, S.
Awarding Body: University College of Swansea
Current Institution: Swansea University
Date of Award: 1996
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Chapter 1 introduces metal-metal bonded compounds and their versatility as reagents in organic synthesis, in particular to their participation in transition metal catalysed reactions across multiple bonds. The problems of borate formation associated with forming a trivalent boron-metal bond is discussed. An approach developed by the author incorporating a degree of steric hindrance around the boron atom in an attempt to synthesise a trivalent boron-metal bond is mentioned. Chapter 1 also reports on the variety of synthetic routes to bimetallic reagents in which the boron and second metal are separated by one, two or three carbon atoms. Chapter 2 introduces the area of carbanion chemistry with particular emphasis on the generation of boron-stabilised carbanions. The reactions of various boron-stabilised carbanions are discussed in detail. Chapter 3 investigates the reactions of four bimetallic species prepared. A sterically hindered base such as mesityllithium will remove a proton α- to the boron thus producing a hetero-substituted boron-stabilised carbanion. The reactions of the carbanion of 1-trimethylsilyl-1-dimesitylborylmethane are dealt with in detail. Reactions such as alkylation, with aromatic aldehydes (which proceed with the presence of boron trifluoride etherate to give the (E)-borylalkene), with other carbonyl compounds and acylation reactions are discussed. The reactions of aromatic aldehydes with the boron-stabilised carbanions derived from 1-phenyldimethylsilyl-1-dimesitylborylmethane and 1-triphenylstannyl-1-dimesitylborylmethane are also mentioned. Finally, the reactions of the allylic boron-stabilised carbanion derived from 1-trimethylsilyl-3-dimesitylborylprop-2-ene with aromatic aldehyde are discussed. Reaction with aromatic aldehydes occurs γ-to the boron atom to give a boryldiene.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available