Addition of thianthrene cation radical to non-conjugated dienes—Part II: Addition to two double bonds

Autor:	Henry J. Shine, Cristina Hofmann, John N. Marx, Kenton H. Whitmire, Anna T. Kelly, Bing Jun Zhao, Teyeb Ould-Ely
Rok vydání:	2006
Předmět:	chemistry.chemical_classification Cation radical Tetrafluoroborate Double bond Diene Activated alumina General Chemistry Conjugated system Photochemistry Medicinal chemistry Adduct chemistry.chemical_compound chemistry Thianthrene
Zdroj:	Journal of Sulfur Chemistry. 27:139-147
ISSN:	1741-6000 1741-5993
Popis:	Reaction of thianthrene cation radical tetrafluoroborate with 1,5-hexadiene, 1,7-octadiene, 1,8-nonadiene and 1,9-decadiene in the molar ratio 4:1 caused addition to occur to one and both of each diene’s double bonds. A mixture of four adducts was thus obtained, namely a bisadduct (12a–d), a monoadduct (13a–d), a di(bis)adduct (14a–d) and a di(mono)adduct (15a–d). The di(mono)adducts (15b–d) were isolated and characterized with 1H and 13C NMR spectroscopy. Under the same condition of excess of cation radical, addition occurred to only one double bond of 1,4-cyclohexadiene and 1,5-cyclooctadiene. Addition to both double bonds was not observed. The bisadduct (16) of 1,4-cyclohexadiene was characterized with 1H and 13C NMR spectroscopy and X-ray crystallography. On activated alumina, 15b–d underwent fast opening of dicationic rings to form mixtures of (E, E) – (17b–d) and (E, Z)-di(5-thianthreniumyl)diene (18b–d) in which the (E, E)-isomer was dominant and was characterized with 1H and 13C NMR spectroscopy.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::5a81afe456f8fb54b42bb52e7a0d2261 https://doi.org/10.1080/17415990600578467 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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