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dc.contributor.authorConnor, Dennis Andrew.en_US
dc.date.accessioned2014-10-21T12:33:39Z
dc.date.available1994
dc.date.issued1994en_US
dc.identifier.otherAAINN93768en_US
dc.identifier.urihttp://hdl.handle.net/10222/55405
dc.descriptionThe photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction forms 1:1:1 adducts of nucleophiles, olefins and electron-poor aromatics. The usual aromatic and nucleophile, thus far in the exploration, are 1,4-dicyanobenzene and methanol in acetonitrile. The transformation proceeds by photoinduced electron transfer to the excited aromatic from the olefin.en_US
dc.descriptionThe potential of the photo-NOCAS reaction to be a synthetic tool has driven studies of the scope and limitations to investigate the intermediate cyclizations of nonconjugated dienes. The interesting dynamics of radical cations and the 1,6-endo, endo cyclization of 2,5-dimethyl-1,5-hexadiene as the radical-cation intermediate of the photo-NOCAS reaction led to the present interest in (R)-(+)-limonene and 2,6-dimethyl-1,6-heptadiene. The photo-NOCAS products of (R)-(+)-limonene are four uncyclized regio- and stereoisomers of photo-NOCAS reaction at the endocyclic double bond. The products of 2,6-dimethyl-1,6-heptadiene are an acyclic photo-NOCAS product, two cyclohexanes (cis and trans) and two cycloheptanes (cis and trans). The cycloheptanes are the products of a 1,7-endo, endo radical-cation cyclization. The cyclohexanes are the results of 1,6-endo cyclization of the intermediate $\beta$-methoxy radical.en_US
dc.descriptionThesis (Ph.D.)--Dalhousie University (Canada), 1994.en_US
dc.languageengen_US
dc.publisherDalhousie Universityen_US
dc.publisheren_US
dc.subjectChemistry, Organic.en_US
dc.titleThe photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reactions of (R)-(+)-limonene and 2,6-dimethyl-1,6-heptadiene.en_US
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dc.contributor.degreePh.D.en_US
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