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Fragmentation of Carbohydrate Anomeric Alkoxy Radicals: A New Synthesis of Chiral 1‐Halo‐1‐iodo Compounds
Author(s) -
González Concepción C.,
Kennedy Alan R.,
León Elisa I.,
RiescoFagundo Concepción,
Suárez Ernesto
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(20010618)40:12<2326::aid-anie2326>3.0.co;2-y
Subject(s) - anomer , alkoxy group , fragmentation (computing) , radical , chemistry , halo , carbohydrate , stereochemistry , organic chemistry , physics , biology , astrophysics , alkyl , galaxy , ecology
One less carbon atom is found in 1‐halo‐1‐iodo compounds obtained by C1−C2 radical fragmentation of carbohydrate 1,2‐halohydrins. This fragmentation is achieved via the anomeric alkoxy radicals of the halohydrins, formed upon reaction with (diacetoxyiodo)benzene and iodine [Eq. (1); X=Cl, Br, I].