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Conformation of C‐1‐Substituted Pyranos‐1‐yl and Pyranosan‐5‐yl Radicals Evidence for a Quasi‐Homo‐Anomeric Stabilization Effect
Author(s) -
Korth HansGert,
Sustmann Reiner,
Praly JeanPierre,
Somsák László
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230532
Subject(s) - chemistry , radical , anomer , anomeric effect , hyperfine structure , bromine , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , physics , quantum mechanics
Acetylated 1‐cyano‐ and 1‐chloro‐pyranos‐1‐yl radicals and 5‐acetoxycarbonyl‐, 5‐methoxycarbonyl‐, and 5‐unsubstituted pyranosan‐5‐yl radicals were generated from the corresponding bromides by bromine abstraction with trimethyltin radicals. The conformation of these radicals, as deduced from the ESR hyperfine splittings, is explained by the combined action of a quasi‐anomeric and a homo‐anomeric stabilization effect. A captodative substitution pattern of the radical center does not influence the conformations.