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http://hdl.handle.net/11375/17977
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DC Field | Value | Language |
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dc.contributor.advisor | McCullough, J. J. | - |
dc.contributor.author | Huang, Chaog-wei | - |
dc.date.accessioned | 2015-08-28T15:51:59Z | - |
dc.date.available | 2015-08-28T15:51:59Z | - |
dc.date.issued | 1969-05 | - |
dc.identifier.uri | http://hdl.handle.net/11375/17977 | - |
dc.description.abstract | The products and mechanisms of some photo-reactions of indenes and naphthalene with acrylonitrile have been studied. Indene reacts with acrylonitrile with the hydrocarbon absorbs light, or when a triplet sensitizer is absorbing. Photolysis under the former condition yields 2-(1-indenyl)- and 2-(3-indenyl)propionitrile, and 6-cyano-2,3-benzobicyclo[3,2,0]hep-2-ene. Base-catalyzed isomerizations of the substituted indenes are reported. On sensitization, cis- and trans-isomers of 7-cyano-2,3-benzobicyclo[3,2,0]hep-2-ene are formed; the known indene dimer is a minor product. Adducts 1,1-dimethyl- and 1,1-diphenylidene with acrylonitrile are also described. Naphthalene adds to acrylonitrile on photolysis to afford trans-8-cyano-2,3-benzobicyclo[4.2.0] octa-2,4-diene and 1- and 2-naphthyl-2-propionitriles. Sensitization gives no detectable products. Studies on fluorescence quenching, solvent effect and deuterium-labelling indicates that exciplexes are formed between acrylonitrile and the excited hydrocarbons. Inter- or intra-molecular protonation of the exciplexes with subsequent reaction of the carbonium ion formed, is suggested to produce indenes or naphthalenes. Possible mechanisms for the formation of other products are proposed. | en_US |
dc.language.iso | en | en_US |
dc.subject | chemistry | en_US |
dc.subject | photo-addition; photolysis | en_US |
dc.subject | indene | en_US |
dc.subject | naphthalene | en_US |
dc.subject | acrylonitrile | en_US |
dc.title | Photo-additions of lndenes and Naphthalene with Acrylonitrile | en_US |
dc.contributor.department | Chemistry | en_US |
dc.description.degreetype | Thesis | en_US |
dc.description.degree | Doctor of Philosophy (PhD) | en_US |
Appears in Collections: | Open Access Dissertations and Theses |
Files in This Item:
File | Description | Size | Format | |
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Huang_Chaog-wei_1969May_PhD.pdf | 25.25 MB | Adobe PDF | View/Open |
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