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Methyl phenyl sulfone, a versatile building block for the construction of chemicals with diverse functionalities
Marc Julia; Dominique Deprez. Syntheses a l'aide de sulfones XIII. Transpositions stereoselectives des alcools α-allyliques β?-sulfones. Tetrahedron Letters. 1976, 17 (4), 277-280.
Gerald W. Buchanan; Cesar Reyes-Zamora; Douglas E. Clarke. A Carbon-13 Nuclear Magnetic Resonance Investigation of Some Substituted Methyl Phenyl Sulfides, Sulfoxides, and Sulfones. Canadian Journal of Chemistry. 1974, 52 (23), 3895-3904.
Factors governing the selective alkylation have been studied. Lithium bases favor dialkylation. For monoalkylation, a potassium base, e.g. KH in THF, should be used: J. Org. Chem., 55, 2234 (1990).
Adds to aldehydes and ketones in the presence of base, e.g. n-BuLi, to give ß-hydroxy sulfones. Conversion of the OH to, e.g. to mesylate, and elimination/desulfurative reduction with sodium amalgam provides a 1-substitued or 1,1-disubstituted alkene by the Julia olefination reaction: Tetrahedron Lett., 4833 (1973); J. Chem. Soc., Perkin 1, 829 (1978). For reaction scheme, see Ethyl phenyl sulfone, A10710. The adducts with aldehydes can also be rearranged to give the dimethyl acetals of the homologous aldehydes: J. Chem. Soc., Perkin 1, 1646 (1978). Reaction with acyl halides gives ß-keto sulfones: J. Org. Chem., 53, 906 (1988).
Gefahrenhinweise (EU): H302
Harmful if swallowed.
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