TIN(II) CHLORIDE CATALYZED ADDITION OF DIAZO SULFONES, DIAZO PHOSPHINE OXIDES, AND DIAZO PHOSPHONATES TO ALDEHYDES.

Article abstract of DOI:10.1016/S0040-4039(00)91877-X

Diazo sulfones, diazo phosphine oxides, and diazo phosphonates add to aldehydes in the presence of a catalytic amounts of tin(II) chloride to yield β-keto sulfones, β-keto phosphine oxides, and β-keto phosphonates, respectively.Reactions with primary aldehydes proceed in higher yields, 53-79percent, than those of secondary aldehydes, 42-56percent.Reactions with tertiary aldehydes, which are more sterically encumbered substrates, give only 5-36percent yields. KEY WORDS: Tin(II) chloride, catalyst, β-keto sulfones, β-keto phosphine oxides, and β-keto phosphonates.