Tetrahedron Letters p. 6583 - 6586 (1992)
Update date:2022-08-17
Topics:
Shine, Henry J.
Yueh, Wang
Cyclohexanol (1), 4-methylcyclohexanol (2), 4-tert-butylcyclohexanol (3), cis-2-methyl- (4) and trans-2-methylcyclohexanol (5) reacted cleanly with thianthrene cation radical perchlorate (Th·+ClO4-) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP). The alcohols were converted quantitatively into cyclohexenes, while Th·+ was converted quantitatively into thianthrene (Th) and thianthrene 5-oxide (ThO). The oxygen atom of ThO came from the alcohol, as was demonstrated with the use of [18O]cyclohexanol.
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