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Ru‐Catalyzed Oxidations with Iodosylbenzene Derivatives. Substituent Effects on Selectivity in Oxidation of Sulfides and Alcohols
Author(s) -
Müller Paul,
Godoy José
Publication year - 1983
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.19830660618
Subject(s) - chemistry , substituent , selectivity , sulfoxide , catalysis , reactivity (psychology) , ring (chemistry) , alcohol oxidation , organic chemistry , carboxylic acid , medicinal chemistry , combinatorial chemistry , medicine , alternative medicine , pathology
Oxidation of sulfides with PhIO/RuCl 2 (PPh 3 ) 3 leads to sulfones. Electronwithdrawing substituents in the aromatic ring of PhIO reduce the reactivity and improves selectivity of the system. Thus, with m ‐iodosylbenzoic acid sulfides are converted to sulfoxide. Under the same conditions aliphatic primary alcohols are transformed to aldehydes with m ‐iodosylbenzoic acid, while PhIO affords carboxylic acids.