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

Bing Jun Zhao, Henry J. Shine, John N. Marx, Anna T. Kelly, Cristina Hofmann, Teyeb Ould-Ely, Kenton H. Whitmire

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)139-147
Number of pages9
JournalJournal of Sulfur Chemistry
Volume27
Issue number2
DOIs
Publication statusPublished - Apr 2006

Keywords

  • Adducts of dienes
  • NMR
  • Thianthrene cation radical

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Addition of thianthrene cation radical to non-conjugated dienes - Part II: Addition to two double bonds'. Together they form a unique fingerprint.

Cite this