Journal of Organic Chemistry p. 3667 - 3672 (1983)
Update date:2022-08-10
Topics:
Olah, George A.
Husain, Altaf
Singh, Brij P.
Mehrotra, Ashok K.
A new, convenient, and inexpensive alternative to the in situ equivalent of iodotrimethylsilane was developed.A mixture of trichloromethylsilane/sodium iodide in dry acetonitrile is found to be a more selective reagent than chlorotrimethylsilane/sodium iodide for the cleavage of ethers, esters, and lactones.Ethers are cleaved regioselectively by this reagent.Cleavage of esters and lactones also occured more readily with the present system.Conversion of alcohols, particularly tertiary and benzylic alcohols, to corresponding iodides is achieved in very short times at ambient temperatures.Deoxygenation of sulfoxides to sulfides is found to be instantaneous.Reductive dehalogenation of alicyclic α-halo ketones to the corresponding ketones has also been studied.The reagent is also used for the deprotection of acetals to carbonyl compounds.
View MoreDoi:10.1007/s13738-016-0864-4
(2016)Doi:10.1002/aoc.5075
(2019)Doi:10.1021/acscatal.5b02116
(2016)Doi:10.1063/1.1726263
(1964)Doi:10.1021/jo00961a014
(1973)Doi:10.1021/j100233a027
(1983)