Kinetic and Stereochemistry of the SO       4    ⊙⊖    ‐Induced Hydroxylation of Cyclohexenes in Aqueous Solution | Zendy

Koltzenburg Günther | Zendy; Bastian Eugenie | Zendy; Steenken Steen | Zendy

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Kinetic and Stereochemistry of the SO 4 ⊙⊖ ‐Induced Hydroxylation of Cyclohexenes in Aqueous Solution

Author(s) -

Koltzenburg Günther,

Bastian Eugenie,

Steenken Steen

Publication year - 1988

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198810661

Subject(s) - hydroxylation , chemistry , aqueous solution , selectivity , hydrolysis , solvent , diffusion , ion , kinetic energy , stereochemistry , medicinal chemistry , organic chemistry , catalysis , enzyme , quantum mechanics , thermodynamics , physics

A largely solvent‐separated ion pair 3 is the presumed intermediate in the hydroxylation of cyclohexenes with SO 4 ⊙⊖ . Radical anions like 1 and 2 are formed in a nearly diffusion‐controlled step. They are subsequently hydrolyzed via 3. The axial/equatorial selectivity of the reaction of H 2 O with 3 is much greater than that observed in the reaction of OH ⊙ with 4‐ tert ‐butylcyclohexene (90:10 vs. 58:42).

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