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Oxidative Cleavage and Rearrangement of Aryl Epoxides Using Iodosylbenzene: on Criegee 's Trail
Author(s) -
Havare Nizam,
Plattner Dietmar A.
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200444
Subject(s) - chemistry , aryl , oxidative cleavage , cleavage (geology) , oxidative phosphorylation , medicinal chemistry , stereochemistry , photochemistry , organic chemistry , catalysis , alkyl , biochemistry , geotechnical engineering , fracture (geology) , engineering
Aryl epoxides undergo rearrangement and oxidative cleavage when reacted with in situ prepared hydroxy‐ λ 3 ‐iodane complexes. The presence of H 2 O plays a decisive role in steering the reaction path. A mechanistic scheme is proposed that accounts for the observed chemoselectivities.