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Differential Cleavage of Arylmethyl Ethers: Reactivity of 2,6‐Dimethoxybenzyl Ethers
Author(s) -
Falck J. R.,
Barma D. K.,
Baati Rachid,
Mioskowski Charles
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010401)40:7<1281::aid-anie1281>3.0.co;2-b
Subject(s) - hydrogenolysis , cleavage (geology) , cleave , chemistry , reactivity (psychology) , medicinal chemistry , catalysis , stereochemistry , organic chemistry , materials science , enzyme , medicine , alternative medicine , pathology , fracture (geology) , composite material
CrCl 2 /LiI selectively cleave benzyl ethers and methoxy‐substituted benzyl ethers (see scheme) in the order: C 6 H 5 CH 2 OR<4‐MeOC 6 H 4 CH 2 OR<3,4‐(MeO) 2 C 6 H 3 CH 2 OR<2,6‐(MeO) 2 C 6 H 3 CH 2 OR. In contrast, C 6 H 5 CH 2 OR is more readily cleaved than 2,6‐(MeO) 2 C 6 H 3 CH 2 OR during catalytic hydrogenolysis while 3,4‐(MeO) 2 C 6 H 3 CH 2 OR is cleaved faster than 2,6‐(MeO) 2 C 6 H 3 CH 2 OR with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ).