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A New Method for the Deprotection of Benzyl Ethers or the Selective Protection of Alcohols
Author(s) -
Madsen Jacob,
Viuf Christel,
Bols Mikael
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000403)6:7<1140::aid-chem1140>3.0.co;2-6
Subject(s) - chemistry , reagent , organic chemistry , substrate (aquarium) , combinatorial chemistry , geology , oceanography
A new selective method for the deprotection of benzyl ethers situated next to alcohols in the α , β , or γ position is presented which uses either NIS or DIB/I 2 as a reagent. After initial formation of a hypoiodite intermediate, the reaction is believed to follow a radical pathway to resemble the Hoffman‐Löffler‐Freytag reaction. The formation of the intermediate hypoiodite is suggested on the basis of NMR studies. Depending on the substrate, the corresponding benzylidene derivatives or diols are isolated.