The synthesis and properties of a benzannelated dihydropyrene and several derivatives

dc.contributor.authorYan, Joseph Shue-Henen_US
dc.date.accessioned2024-08-15T20:19:02Z
dc.date.available2024-08-15T20:19:02Z
dc.date.copyright1978en_US
dc.date.issued1978
dc.degree.departmentDepartment of Chemistry
dc.degree.levelMaster of Science M.Sc.en
dc.description.abstractIn this work we have synthesised a symmetrical benzanne­lated dimethyldihydropyrene and s.h0vm that it is aromatic both in terms of magnetic effects (diatropic and large 'Q' value) and classical reaction chemistry (in that it U1.1de rgce3 electrophilic substitution reactions). Synthetic procedures have been developed which allow a base-induced sulphinic acid elimination as an alter­native to the better-known Hofmann type sulphonium salt elimina­tion in the last step of the sequence to produce cyclophane-dienes. Also a method has been found whereby alkyl substituents may be introduced onto the bridge position of the phane-diene. The synthesis of the first terphenylophane is also described . The phototautomerisation of the benzodimethyldihydropyrene and its derivatives has been studied, and it is found that the activation barriers between the phane-diene=dihydropyrene tau­tomers are somewhat higher (i.e. process is slower) than for the parent system. The barriers to rotation in several substituted terphenyls have also been determined.en_US
dc.format.extent122 pages
dc.identifier.urihttps://hdl.handle.net/1828/20226
dc.rightsAvailable to the World Wide Weben_US
dc.titleThe synthesis and properties of a benzannelated dihydropyrene and several derivativesen_US
dc.typeThesisen_US

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