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Title: The synthesis of nitrogen-containing compounds via organoboranes and organoborates
Author: Paget, W. E.
Awarding Body: University College of Swansea
Current Institution: Swansea University
Date of Award: 1981
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Chapter I: This section of the thesis is a short review of the literature for the period January 1978 to March 1979 which includes many important developments in organoboron chemistry. Chapter II: This section records the reaction of N,N-dimethylmethyleneimnonium iodide as an electrophile with trialkylalkynylborate salts in an attempt to synthesise variously substituted N,N-dimethylallylamines and also attempts to generalise the approach to synthesising nitrogen compounds from organoborates. The limitations of the reaction are discussed along with evidence for the stereochemistry of the products, and the reaction is compared briefly with other well documented cases. A literature report for the synthesis of N044-dimethylmethyleneinmonium trifluoracetate is also proved to be erroneous. Chapter III: This section deals with various attempts at synthesising nitrogen-containing compounds via direct migration of an alkyl group from boron to nitrogen. N-chloro-N-sodiourethane was found to give acceptable yields of N-alkylurethanes (based on one alkyl group migration) for tri-n-primary alkylboranes. Yields fell considerably for secondary alkyl groups and further work was discontinued due to the unstable nature of the salt. Chapter IV: This section records the results of the reaction of diaryl(2-aminoethoxy)-boranes with both molecular bromine and N-bromosuccinimide to yield brominated and non-brominated biaryl products. The yields are moderate and limited to boranes which contain a thienyl group. The remarkable reactivity and uniqueness of bromine and N-bromosuccinimide as promoting electrophiles are discussed, together with some ideas for future prospects. Chapter V: This section deals with the high yield synthesis of a novel organoborane type 5-diisopropyliminio-2,2,4,4,-tetraphenyl-2,4-diborata-l-oxa-3-oxoniacylopentane resulting from attempted synthesis of an acylborane. Evidence for the structure is presented also with possible mechanisms for its formation. Unique complexes are formed with various donor compounds, and these are listed and possible structures discussed.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available