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Synthesis 1997; 1997(2): 217-220
DOI: 10.1055/s-1997-1158
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Some Unusual Reactions of 3,5-Di-tert-butyl-1,2-dithiolium Perchlorate with Nucleophiles

Klaus Hartke* , Andreas Kraska
  • *Institut für Pharmazeutische Chemie, Universität Marburg, Marbacher Weg 6, D-35032 Marburg/Lahn, Germany, Fax +49(6421)288994
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Publication Date:
31 December 2000 (online)

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3,5-Di-tert-butyl-1,2-dithiolium perchlorate (4) reacts with ethanol, piperidine or metal cyclopentadienides by carbophilic attack to form the addition products 2, 3 and 5 at the sterically hindered 3-position. Methyl- and phenyllithium cleave the 1,2-dithiolium ring in 4 by thiophilic attack giving rise to the β-methylthio- or (β-phenylthio)prop-2-enones 7 a, b. Nitromethane condenses with 4 in a complex reaction sequence to furnish the β-cyanoprop-2-enone 12.

3,5-di-tert-butyl-1,2-dithiolium perchlorate - 3,3-disubstituted 3H-1,2-dithioles - metal cyclopentadienides - β-cyanopropen-2-one