Electronic Effects in Olefin Oxidation by Imidoosmium( VIII ) Compounds | Zendy

Muñiz Kilian | Zendy

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Electronic Effects in Olefin Oxidation by Imidoosmium( VIII ) Compounds

Author(s) -

Muñiz Kilian

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200300774

Subject(s) - chemistry , steric effects , reactivity (psychology) , electrophile , osmium , nucleophile , olefin fiber , electronic effect , reagent , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , catalysis , ruthenium , medicine , alternative medicine , pathology

Imido osmium( VIII ) complexes are versatile oxidants for C−C double bond functionalisation. Despite their structural similarity with OsO 4 their reactivity cannot always be compared with this seminal reagent. Detailed investigations including kinetic competition experiments are presented that uncover the electronic and steric preferences of osmium imido complexes. The different behaviour of OsO 4 and its imido derivatives towards tertiary amines and diamines is clarified. Hammett correlation studies reveal that the reactivity spectrum of the respective oxidants ranges from a strongly electrophilic behaviour in the case of OsO 4 to a rather nucleophilic character as encountered for OsO(N t Bu) 3 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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