Journal of the Chemical Society. Perkin transactions I p. 3070 - 3073 (1981)
Update date:2022-07-30
Topics:
McCrindle, Robert
McAlees, Alan J.
Stephenson, Donald K.
Enol ethers of dialkylacetaldehydes, either as such, or generated in situ from the corresponding acetals, undergo ready methylthiomethylation when heated with dimethyl sulphoxide-acetic anhydride (or methylthiomethyl acetate) in the presence of boron trifluoride-diethyl ether.These same reagent combinations can be used to methylthiomethylate certain activated aromatic compounds.The synthetic utility of the former reaction is demonstrated in the synthesis of 2,2,6,6-dimethyl-4-thiaheptanedial (4) which has been converted into 3,3,7,7,11,11,15,15-octamethyl-1,9-dithia-5,13-diazacyclohexadecane (7).
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