@article{camaggi_photochemical_1971,
	title = {Photochemical isomerisation derivatives of decafluorocyclohexene and their reactions},
	url = {http://dx.doi.org/10.1039/J39710000925},
	doi = {10.1039/J39710000925},
	abstract = {Perfluoro-(methylenecyclopentane) and -(1-methylcyclopentene), together with some higher-boiling compounds, have been obtained by the u.v.-irradiation of decafluorocyclohexene. Perfluoro-(methylenecyclopentane) underwent addition of chlorine and isomerisation to perfluoro-(1-methylcyclopentene), catalysed by fluoride ion; on treatment with sodium borohydride in bis-(2-methoxyethyl) ether it gave 1-hexafluoro-2-methylcyclopentene, 3,3,4,4-tetrafluoro-1-trifluoromethylcyclopentene, and five polyfluoro-olefins as minor components. Both perfluoro-(methylenecyclopentane) and -(1-methylcyclopentene), on treatment with sodium iodide in acetone, afforded hexafluoro-1-iodo-2-trifluoromethylcyclopentene, which reacted with magnesium in ether to give a Grignard reagent, and with pentafluoroiodobenzene and copper bronze to give perfluoro-(2,2[prime or minute]-dimethylbicyclopent-1,1[prime or minute]-enyl) and hexafluoro-1-pentafluorophenyl-2-trifluoromethylcyclopentene. Perfluoro-(methylenecyclopentane) reacted with aluminium chloride in methyl iodide to give 1-(chlorodifluoromethyl)heptafluorocyclopentene, which, on treatment with sodium iodide in acetone, afforded 1-(difluoroiodomethyl)heptafluorocyclopentene. Both compounds could be dehalogenofluorinated to give perfluoro-(3-methylenecyclopentene), which added chlorine and underwent isomerisation, catalysed by fluoride ion, to perfluoro-1- and -2-methylcyclopentadiene. When heated, the former compound gave perfluoro-(1,4-dimethyltricyclo[5,2,1,0]deca-3,8-diene), a Diels-Alder dimer, and the latter gave a mixture of dimeric products. From the high-boiling products of the irradiation of decafluorocyclohexene, perfluoro-bicyclohex-1,1[prime or minute]-enyl, -1-cyclohexylcyclohexene, -1,1[prime or minute]-bicyclohexylidene, -1-(cyclohex-1-enyl)-1-methylcyclopentane, -bicyclohexyl, and -1-cyclohexyl-1-methylcyclopentane, were obtained.},
	number = {0},
	journal = {Journal of the Chemical Society C},
	author = {Camaggi, G and Gozzo, F},
	year = {1971},
	note = {Publisher: The Royal Society of Chemistry
ISBN: 0022-4952},
	pages = {925--936},
}

{"_id":"pJdRxoD4npiAu72Mx","bibbaseid":"camaggi-gozzo-photochemicalisomerisationderivativesofdecafluorocyclohexeneandtheirreactions-1971","author_short":["Camaggi, G","Gozzo, F"],"bibdata":{"bibtype":"article","type":"article","title":"Photochemical isomerisation derivatives of decafluorocyclohexene and their reactions","url":"http://dx.doi.org/10.1039/J39710000925","doi":"10.1039/J39710000925","abstract":"Perfluoro-(methylenecyclopentane) and -(1-methylcyclopentene), together with some higher-boiling compounds, have been obtained by the u.v.-irradiation of decafluorocyclohexene. Perfluoro-(methylenecyclopentane) underwent addition of chlorine and isomerisation to perfluoro-(1-methylcyclopentene), catalysed by fluoride ion; on treatment with sodium borohydride in bis-(2-methoxyethyl) ether it gave 1-hexafluoro-2-methylcyclopentene, 3,3,4,4-tetrafluoro-1-trifluoromethylcyclopentene, and five polyfluoro-olefins as minor components. Both perfluoro-(methylenecyclopentane) and -(1-methylcyclopentene), on treatment with sodium iodide in acetone, afforded hexafluoro-1-iodo-2-trifluoromethylcyclopentene, which reacted with magnesium in ether to give a Grignard reagent, and with pentafluoroiodobenzene and copper bronze to give perfluoro-(2,2[prime or minute]-dimethylbicyclopent-1,1[prime or minute]-enyl) and hexafluoro-1-pentafluorophenyl-2-trifluoromethylcyclopentene. Perfluoro-(methylenecyclopentane) reacted with aluminium chloride in methyl iodide to give 1-(chlorodifluoromethyl)heptafluorocyclopentene, which, on treatment with sodium iodide in acetone, afforded 1-(difluoroiodomethyl)heptafluorocyclopentene. Both compounds could be dehalogenofluorinated to give perfluoro-(3-methylenecyclopentene), which added chlorine and underwent isomerisation, catalysed by fluoride ion, to perfluoro-1- and -2-methylcyclopentadiene. When heated, the former compound gave perfluoro-(1,4-dimethyltricyclo[5,2,1,0]deca-3,8-diene), a Diels-Alder dimer, and the latter gave a mixture of dimeric products. From the high-boiling products of the irradiation of decafluorocyclohexene, perfluoro-bicyclohex-1,1[prime or minute]-enyl, -1-cyclohexylcyclohexene, -1,1[prime or minute]-bicyclohexylidene, -1-(cyclohex-1-enyl)-1-methylcyclopentane, -bicyclohexyl, and -1-cyclohexyl-1-methylcyclopentane, were obtained.","number":"0","journal":"Journal of the Chemical Society C","author":[{"propositions":[],"lastnames":["Camaggi"],"firstnames":["G"],"suffixes":[]},{"propositions":[],"lastnames":["Gozzo"],"firstnames":["F"],"suffixes":[]}],"year":"1971","note":"Publisher: The Royal Society of Chemistry ISBN: 0022-4952","pages":"925–936","bibtex":"@article{camaggi_photochemical_1971,\n\ttitle = {Photochemical isomerisation derivatives of decafluorocyclohexene and their reactions},\n\turl = {http://dx.doi.org/10.1039/J39710000925},\n\tdoi = {10.1039/J39710000925},\n\tabstract = {Perfluoro-(methylenecyclopentane) and -(1-methylcyclopentene), together with some higher-boiling compounds, have been obtained by the u.v.-irradiation of decafluorocyclohexene. Perfluoro-(methylenecyclopentane) underwent addition of chlorine and isomerisation to perfluoro-(1-methylcyclopentene), catalysed by fluoride ion; on treatment with sodium borohydride in bis-(2-methoxyethyl) ether it gave 1-hexafluoro-2-methylcyclopentene, 3,3,4,4-tetrafluoro-1-trifluoromethylcyclopentene, and five polyfluoro-olefins as minor components. Both perfluoro-(methylenecyclopentane) and -(1-methylcyclopentene), on treatment with sodium iodide in acetone, afforded hexafluoro-1-iodo-2-trifluoromethylcyclopentene, which reacted with magnesium in ether to give a Grignard reagent, and with pentafluoroiodobenzene and copper bronze to give perfluoro-(2,2[prime or minute]-dimethylbicyclopent-1,1[prime or minute]-enyl) and hexafluoro-1-pentafluorophenyl-2-trifluoromethylcyclopentene. Perfluoro-(methylenecyclopentane) reacted with aluminium chloride in methyl iodide to give 1-(chlorodifluoromethyl)heptafluorocyclopentene, which, on treatment with sodium iodide in acetone, afforded 1-(difluoroiodomethyl)heptafluorocyclopentene. Both compounds could be dehalogenofluorinated to give perfluoro-(3-methylenecyclopentene), which added chlorine and underwent isomerisation, catalysed by fluoride ion, to perfluoro-1- and -2-methylcyclopentadiene. When heated, the former compound gave perfluoro-(1,4-dimethyltricyclo[5,2,1,0]deca-3,8-diene), a Diels-Alder dimer, and the latter gave a mixture of dimeric products. From the high-boiling products of the irradiation of decafluorocyclohexene, perfluoro-bicyclohex-1,1[prime or minute]-enyl, -1-cyclohexylcyclohexene, -1,1[prime or minute]-bicyclohexylidene, -1-(cyclohex-1-enyl)-1-methylcyclopentane, -bicyclohexyl, and -1-cyclohexyl-1-methylcyclopentane, were obtained.},\n\tnumber = {0},\n\tjournal = {Journal of the Chemical Society C},\n\tauthor = {Camaggi, G and Gozzo, F},\n\tyear = {1971},\n\tnote = {Publisher: The Royal Society of Chemistry\nISBN: 0022-4952},\n\tpages = {925--936},\n}\n\n","author_short":["Camaggi, G","Gozzo, F"],"key":"camaggi_photochemical_1971","id":"camaggi_photochemical_1971","bibbaseid":"camaggi-gozzo-photochemicalisomerisationderivativesofdecafluorocyclohexeneandtheirreactions-1971","role":"author","urls":{"Paper":"http://dx.doi.org/10.1039/J39710000925"},"metadata":{"authorlinks":{}},"html":""},"bibtype":"article","biburl":"https://bibbase.org/zotero/kjelljorner","dataSources":["64RFiGdCa5JLg5kLH"],"keywords":[],"search_terms":["photochemical","isomerisation","derivatives","decafluorocyclohexene","reactions","camaggi","gozzo"],"title":"Photochemical isomerisation derivatives of decafluorocyclohexene and their reactions","year":1971}