Thesis-1997-Normansell.pdf (1.48 MB)
Download fileSynthetic studies towards methylene cyclic sulfamidites and sulfamidates
thesis
posted on 2018-02-27, 15:10 authored by Frances M. NormansellChapter one provides a general introduction, which reviews relevant literature
concerning the preparation and chemistry of cyclic sulfamidites and sulfamidates. A
comparison is drawn between these compounds and the analogous cyclic sulfites,
cyclic sulfates, epoxides and aziridines, in terms of their chemistry. Work undertaken
by other members of the research group in this area is discussed and a review of the
preparation of allene oxides and methyleneaziridines is given. Project aims, in terms
of the preparation of a methylene cyclic sulfamidate are discussed in relation to the
successful preparation of a methylene cyclic sulfite within our group.
Chapter two describes the preparation of a simple cyclic sulfamidate and goes on to
detail three routes undertaken towards the synthesis of novel 4-methylene cyclic
sulfamidates. The first approach involved subjecting a β-hydroxy-imine to the
conditions used to convert an amino alcohol to a cyclic sulfite, which unexpectedly
did not result in formation of the desired 4-methylene cyclic sulfamidite. An
alternative route for the preparation of 4-methylene cyclic sulfamidites was explored
using an elimination reaction employing selenoxides to introduce the double bond as
the final synthetic step. We successfully completed the synthesis of two precursors
possessing different substituents attached to the selenium atom, although neither
could be successfully eliminated to the desired methylene cyclic sulfamidite.
Chapter three describes the detailed experimental work undertaken in this thesis.
Funding
EPSRC.
History
School
- Science
Department
- Chemistry
Publisher
© Frances NormansellPublisher statement
This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 2.5 Generic (CC BY-NC-ND 2.5) licence. Full details of this licence are available at: http://creativecommons.org/licenses/by-nc-nd/2.5/Publication date
1997Notes
A Master's Thesis. Submitted in partial fulfilment of the requirements for the award of Master of Philosophy at Loughborough University.Language
- en