Functionalization of polyisobutylene, and, Synthesis and crystal structure of heterocyclic quinoimines.
AdvisorHall, Jr., H.K.
MetadataShow full item record
PublisherThe University of Arizona.
RightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
AbstractPart I. Functionalization of polyisobutylene. Polyisobutylene(PIB), a large-scale commercial polymer, is of potential interest as the component of block copolymers with unique physical properties. Lochmann and Schlosser used super bases, a combination of n-BuLi and KOtBu, to abstract allylic hydrogens from simple olefins to give anions. We applied this super-base chemistry to PIB to introduce new functional groups, such as carboxylic acid, esters, and amino groups, into the polymer. The functionalization of PIB via PIB-Li, formed by reaction with the base, led to complications because the PIB-Li was too reactive and basic. PIB carboxylic acid was obtained by the reaction of PIB heterocuprate with carbon dioxide without any complications. Part II. Synthesis and crystal structure of heterocylic quinoimines. Various heterocyclic quinones which have oxazole rings as their component were synthesized. The transformation to the quinoimines was achieved by the reaction of quinones and triphenylarsinimines which were prepared by the reaction of triphenylarsine oxide and isocyanates. X-Ray analyses of quinoimines showed that the molecules were not planar. The arylimino groups were out of the plane of the molecule. Each quinoimine had an unique crystal structure.