70061-62-0Relevant articles and documents
Expanding the scope of methyl xanthate esters - From Barton-McCombie reaction auxiliary to versatile protective group
Thorsheim, Karin,Manner, Sophie,Ellervik, Ulf
supporting information, p. 6329 - 6333 (2017/09/29)
The methyl xanthate ester is presented as a versatile protective group for alcohols. Hydroxyl groups can easily be transformed into methyl xanthate esters by several methods and are commonly used as an auxiliary in the Barton-McCombie reaction. We show that these methyl xanthate esters can readily and chemoselectively be cleaved under mild conditions by the action of diethylenetriamine using microwave heating. This method is orthogonal to many common hydroxyl protective groups that can be introduced and cleaved in the presence of methyl xanthate ester.
Facile Barton-McCombie deoxygenation of alcohols with tetrabutylammonium peroxydisulfate and formate ion
Hee, Sock Park,Hee, Yoon Lee,Yong, Hae Kim
, p. 3187 - 3190 (2007/10/03)
(Chemical Equation Presented) A new method for efficient radical deoxygenation of alcohols is described for preparing bulk chemicals avoiding scale-up problems. Treatment of various thiocarbonyl derivatives with (Bu 4N)2S2O8 and HCO2Na in DMF afforded the corresponding deoxygenated products in excellent yields. The deoxygenation appears to be initiated by the transfer of a single electron to thiocarbonyl derivatives from CO2?- rather than from SO4?-.
