Journal of Organic Chemistry p. 4458 - 4462 (1989)
Update date:2022-08-03
Topics:
Krishnamurthy, S.
Aimino, D.
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 deg C) and can tolerate a wide variety of functional groups, such as halogen, nitro, carboxylic acid, and their derivatives.The presence of electron-withdrawing substituents dramatically enhances the rate of reduction (p-chlorophenyl disulfide is quantitatively reduced in 30 s) and electron-releasing substituents diminishes the rate of cleavage.The reaction is sensitive to steric effects (2,4-di-tert-pentylphenyl disulfide underwent 25percent reduction in 24 h).However, such hindered disulfides can be rapidly and quantitatively reduced in refluxing THF.The reaction of LTBA with alkyl disulfides is extremely sluggish.The reaction provides a useful and simple means for the facile and selective reduction of aromatic disulfides where this is required in synthetic operations.
View MoreYancheng Smiling Imp & Exp Co., Ltd.
Contact:+86-515-83173586
Address:Rm1207, BLD#03, Phoenix Plaza, Juheng Road, Yancheng, Jiangsu, P.R. China
Guangxi Bonger Pharmaceutical Co., Ltd
website:http://napo.lookchem.com/
Contact:+86-18817331185
Address:Donghai Industrial Zone, Tiandong Country,Guangxi,China
Jinan Yijialian Economic and Trade Development Co., Ltd.
Contact:+86 0531-66729596
Address:jinan
Contact:+86-571-28186845
Address:Room 1224,Eastcom Mansion,398 Wensan Road,Hangzhou,310013 China
Zibo Fuxi'er Chemical Co.,Ltd (Shanxian Fuxi'er Chemical Co.,Ltd)
Contact:+86-533-2091422
Address:Eastern 4 on the 3th Road ,Liangxiang Industrial Park, Zibo city ,Shandong,China
Doi:10.1021/jm020819i
(2002)Doi:10.1021/jm00365a014
(1983)Doi:10.1002/anie.200501665
(2005)Doi:10.1021/om0505817
(2005)Doi:10.1021/jo952263v
(1996)Doi:10.1515/HC.2005.11.5.433
(2005)