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 MoreHENAN NEW BLUE CHEMICAL CO.,LTD
website:http://www.newbluechem.com
Contact:86-371-55170693/55170694
Address:Zhengzhou International Trade New Territory,Jinshui District,Zhengzhou ,China
Beijing Stable Chemcial Co.ltd
Contact:86-10-63785052
Address:A1301 Technological Edifice. No.4 FuFeng Road,FengTai District, Beijing. China
Tianjin Chemsyntech Chemical Co., Ltd
Contact:+86-22-60872258
Address:Haitai green industry base in Tianjin, K1,5-601
Suzhou Credit International Trading Co., Ltd
Contact:+86-512-65398039
Address:Qingdeng, Hightech. District, Suzhou
Contact:0086-22-2822 1962 / 2822 1963
Address:B-808, No. 1, North-South Street, Hexi District,
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)