Reductive Lithiation of Some Thioketals Using Lithium 1-(Dimethylamino)naphthalenide

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The stability of the reducing agent above -45° in the catalytic procedure may be due to the far shorter average lifetime of the radical anions or to the absence of the dianion which could be the species that loses the dimethylamide anion

In the catalytic method, completion of reduction can be readily determined visually; the dark red color of the sulfur-stabilized anion is replaced by the green-black color of the radical anion

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