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[摘要]：Aryl(chloro)methyl 4-tolyl sulfoxides were synthesized from arylmethyl 4-tolyl sulfoxides in moderate-to-good yields by sequential treatment with lithium diisopropylamide and tosyl chloride at low temperatures. Treatment of the lithium alpha-sulfinyl carbanion of the aryl(chloro)methyl 4-tolyl sulfoxides with aldehydes or ketones resulted in the formation of adducts in good-to-high yields. Treatment of these adducts with tert-butylmagnesium chloride gave the corresponding magnesium alkoxides. On treatment with isopropylmagnesium chloride, the alkoxides gave the corresponding magnesium beta-oxido carbenoids, which rearranged to give alpha-aryl ketones in good-to-high yields. The magnesium enolate intermediates generated by rearrangement of the beta-oxido carbenoids could also be trapped with electrophiles to give alpha-aryl alpha-substituted ketones. These procedures offer a good method for the synthesis of a variety of alpha-aryl ketones from aldehydes and ketones. |
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