Attempted protonation of cyclobutane with H2SO4-t or CF3COOH-t failed to give any open chain butyl product as evidence for the formation of protonated cyclobutane. The treatment of cyclobutane with an excess of CF3SO3H-t in a sealed tube at 75 °C for 3 days followed by hydrolysis did give rise to the four isomeric butyl alcohols containing some T-label in the butyl groups. The upper limit for this ring cleavage, probably via protonated cyclobutane, was about 1%. H–T exchange in the recovered cyclobutane was also observed.
An attempted solvolytic demercuration of triphenylvinylmercuric acetate or bromide (1-HgOAc or 1-HgBr) in HOAc in the presence of HClO4 failed to give the triphenylvinyl cation, but instead gave a high yield of triphenylethylene (2). Kinetic studies showed that the formation of 2 from the reaction of 1-HgOAc with HClO4 in CH3OH was first order with respect to the substrate and second order with respect to HClO4. Mechanistic implications of these findings are discussed.
Während die Reaktion mit tritiierter Schwefel‐ oder Trifluoressigsäure keine Anzeichen für eine Protonierung des Cyclobutans liefert, entstehen im Bombenrohr bei 75°C mit tritiierter Tri?uonnethansulfonsäure (nach Hydrolyse) ‐ über die entsprechenden Sulfonate ‐ isomere Butanole, die vermutlich über protonierte Cyclobutane gebildet werden.
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