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Green chemistry: polychelatogens for water purification and the development of an organocatalytic enantioselective [1,2]-Stevens rearrangement
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Masand, Shruti A.. Green chemistry: polychelatogens for water purification and the development of an organocatalytic enantioselective [1,2]-Stevens rearrangement. Retrieved from https://doi.org/doi:10.7282/t3-4czw-ed26

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TitleGreen chemistry: polychelatogens for water purification and the development of an organocatalytic enantioselective [1,2]-Stevens rearrangement
NameMasand, Shruti A. (author); Brenner-Moyer, Stacey (chair); Galoppini, Elena (member); He, Huixin (member); Schulz, Michael D (member); Rutgers University; Graduate School - Newark
Date Created2022
Other Date2022-10 (degree)
SubjectChemistry, Organic chemistry, Polymer chemistry, Water -- Purification, Drinking water
Extent256 pages : illustrations
DescriptionNitrogen and sulfur ylides find extensive use in synthetic organic chemistry. N-allyl and -benzyl ylides are prone to [2,3]-rearrangement and the competing [1,2]- rearrangement (or Steven’s rearrangement). In contrast to the [2,3]-sigmatropic rearrangement, a catalytic asymmetric variant of the Stevens rearrangement of N-allyl or -benzyl ylides remains elusive, and the reaction mechanism has been debated in the literature since the 1950‘s. Diastereoselective versions of Steven’s 1,2-rearrangements have been exploited in synthesis to establish complex polycyclic backbones of alkaloids but require preinstallation of chiral centers. A catalytic enantioselective Steven’s rearrangement of N-allyl or -benzyl ammonium ylides would circumvent this requirement, thereby revolutionizing alkaloid synthesis. Chapter one describes the recent developments in [1,2]-Stevens rearrangement. Chapter two of this thesis describes efforts towards successfully developing an organocatalytic enantioselective [1,2]-Stevens rearrangement.
Considering the present demands for potable water around the world and even in this country, the need for technologies to improve water quality has never been more important. In this context, chapter three describes the synthesis of a polychelatogen derived from bio-renewable lactide. It is a water-soluble polythioether containing hydroxy and carboxylate chelating groups that aid in binding to heavy metals like lead. Additionally, it was observed that its binding is not affected by the presence of metal cations such as Na+, K+, Ca2+, which are commonly found in drinking water sources. Using Grubbs third generation catalyst, we can obtain polymers with controlled molecular weights. Interestingly, the kinetics of polymerization is stereochemistry dependent. The binding capacity to other heavy metals such as Ni2+, Zn2+, Cd2+ and Cr6+ was studied at pH 6 and both polymers demonstrated good binding to all metals except Cr6+. This technology can be extended to the use of polymer resins and may find future use in water purification.
NotePh.D.
NoteIncludes bibliographical references
Genretheses
Persistent URLhttps://doi.org/doi:10.7282/t3-4czw-ed26
LanguageEnglish
CollectionGraduate School - Newark Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.
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