REGIOSELECTIVITY OF METALATION OF 1,3-DITHIOLANES AND 1,3-DITHIOLANE 1-OXIDES |
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| Authors: | Francis A Carey Oliver D Dailey Jr |
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| Institution: | Department of Chemistry , University of Virginia , Charlottesville , Virginia , 22901 , U.S.A. |
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| Abstract: | Abstract Deprotonation of 1,3-dithiolane 1-oxide (3) and trans-2-phenyl-1,3-dithiolane 1-oxide (5) leads to cleavage of the derived anions. Cleavage reactions do not occur with trans-hexahydro-1,3-benzodithiole (7), its 1-oxide, or its 1,1-dioxide all of which can be metalated and alkylated quantitatively at C-2. The preparation and reactions of the sulfoxides derived from 7 are not highly stereoselective. |
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