Rapid and selective reduction of functionalized aromatic disulfides with lithium tri-tert-butoxyaluminohydride. A remarkable steric and electronic control. Comparison of …

S Krishnamurthy, D Aimino

Index: Krishnamurthy, S.; Aimino, D. Journal of Organic Chemistry, 1989 , vol. 54, # 18 p. 4458 - 4462

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Citation Number: 37

Abstract

Lithium tri-tert-butoxyaluminohydride (LTBA), an exceptionally mild reducing agent in organic synthesis, reduces functionalized aromatic disulfides to the corresponding thiols in quantitative yield. The reaction is rapid (for example, o-tolyl disulfide is reduced to completion in 60 min at 25" C) and can tolerate a wide variety of functional groups, such as halogen, nitro, carboxylic acid, and their derivatives. The presence of electron- ...