Characterization of Monomeric Thiopivaldehyde

Article abstract of DOI:10.1021/ja00271a030

The title compound is the first aliphatic thioaldehyde to be observed under odinary laboratory conditions.Its spectral data and chemical characterization are described, including 2+3 cycloadditions with nitronate ester 6, 2+4 cycloaddition with reactive dienes, thiophilic addition with phenyllithium, carbophilic addition with butyllithium, conversion to episulfide 15 by the Wittig reagent, and oxidation to sulfine 17 with MCPBA.Independent generation of thiopivaldehyde from tert-butyllithium + ethyl thionoformate followed by heating 9 in xylene or by cycloreversion of 2-tert-butyl-1,2-dithiolane with butyllithium are also described.