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The reaction of 1,n-bis(phenylsulfanyl)alkanes 1 (n = 2-6) with an excess of lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB; 2.5 mol %) in the presence of a carbonyl compound (PhCHO, Et2CO; Barbier conditions), in THF at -78 oC leads, after hydrolysis with water, to the expected 1,(n+2)-diols 6, yields being < 19% for n = 2 and in the range of 31-78% for n = 3-6. When the lithiation is performed in a two-step process (Grignard conditions), first with the same lithiating reagent and then with different carbonyl compounds (Bu t CHO, PhCHO, PhCH2CHO, Et2CO, (CH2)5CO, (CH2)7CO, (-)-menthone, Ph2CO), diols 6 are obtained in significant lower yields except for 1,3-bis(phenylsulfanyl)propane 1 (n = 3).

1,n-Bis(phenylsulfanyl)alkanes as precursors of 1,n-dilithio compounds: synthesis of diols