Synthetic studies towards panacene : a thesis presented in partial fulfilment of the requirements for the degree of Master of Science in Chemistry at Massey University

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dc.contributor.authorGibson, Jennifer Joy
dc.date.accessioned2019-02-13T01:19:57Z
dc.date.available2019-02-13T01:19:57Z
dc.date.issued1987
dc.description.abstractSYNTHETIC STUDIES TOWARDS PANACENE (1) 2-Trimethylsilyloxyfuran (l}) and 2-acetyl-1 ,4-benzoquinone (6) were prepared according to published methods. The uncatalysed addition of 2-trfmethylsilyloxyfuran (23) to the quinone (6) gave cis-3a,8b-dihydro-8-acetyl-7-hydroxyfuro­ [3,2-b]benzofuran-2-(3H)-one (24) in 50% yield. The reaction of other 1,4-benzoquinones was investigated, establishing the necessity of an activating substituent at C-2 of the quinone. Attempts to reduce the acetyl group of cis-3a,8b-dihydro-8- -acetyl-7-hydroxyfuro[3,2-b]benzofuran-2-(3H)-one (24) to the ethyl group present in Panacene (l) were unsuccessful, although reduction of the ketone with sodium borohydride gave cis-3a,8b-dihydro-8-(1 '-hydroxyethyl)-7-hydroxyfuro[3,2-b]­ benzofuran-2-(3H)-one (51). The conversion of cis-3a,8b-dihydro-8-acetyl-7-hydroxyfuro­ [3,2-b]henzofuran-2-(3H)-one (24) to cis-3,3a,9b-trihydro- 5-hydroxy-5-methylfuro[3,2-c][2]benzopyran-2,6,9-(5H)-trione (58) was carried out using cerie ammonium nitrate.en_US
dc.identifier.urihttp://hdl.handle.net/10179/14251
dc.language.isoenen_US
dc.publisherMassey Universityen_US
dc.rightsThe Authoren_US
dc.subjectOrganic compoundsen_US
dc.subjectSynthesisen_US
dc.subjectOrganohalogen compoundsen_US
dc.subjectPanaceneen_US
dc.titleSynthetic studies towards panacene : a thesis presented in partial fulfilment of the requirements for the degree of Master of Science in Chemistry at Massey Universityen_US
dc.typeThesisen_US
massey.contributor.authorGibson, Jennifer Joy
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorMassey Universityen_US
thesis.degree.levelMastersen_US
thesis.degree.nameMaster of Science (M. Sc.)en_US
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