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Trichloro(methyl)silane/Sodium Iodide, A New Regioselective Reagent for the Cleavage of Ethers
Author(s) -
Olah George A.,
Husain Altaf,
Gupta B. G. Balaram,
Narang Subhash C.
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198106901
Subject(s) - regioselectivity , reagent , acetonitrile , silane , chemistry , methyl iodide , sodium iodide , alkyl , cleavage (geology) , primary (astronomy) , organic chemistry , medicinal chemistry , sodium , polymer chemistry , catalysis , materials science , physics , astronomy , fracture (geology) , composite material
More than a dozen examples verify that ethers are cleaved regioselectively in very good yields by MeSiCl 3 /NaI in acetonitrile; primary and secondary methyl‐, benzyl‐, trityl‐ and tetrahydropyranyl ethers directly afford the primary and secondary alcohols. In the case of tert ‐alkylmethyl ethers only the tert ‐alkyl iodides are formed.