The Acid‐catalyzed Hydrolysis of CF 3 ‐deactivated Diazoalkanes | Zendy

Dahn Hans | Zendy; Lenoir John Henri | Zendy

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The Acid‐catalyzed Hydrolysis of CF 3 ‐deactivated Diazoalkanes

Author(s) -

Dahn Hans,

Lenoir John Henri

Publication year - 1979

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.19790620719

Subject(s) - chemistry , solvolysis , protonation , catalysis , kinetic isotope effect , nucleophile , hydrolysis , acid catalysis , medicinal chemistry , solvent , proton , kinetic energy , ion , photochemistry , deuterium , organic chemistry , physics , quantum mechanics

The acid‐catalyzed hydrolysis of CF 3 CHN 2 ( 1 ) follows an A 2 mechanism of preequilibrium protonation and rate‐determining solvolysis of the intermediate diazonium ion 4 ; this was demonstrated by: (a) the inverse kinetic isotope effect; (b) H‐D exchange; (c) the unimportance of general acid catalysis; (d) strong rate acceleration by added nucleophiles. The activation parameters have been determined in two solvent systems. In contrast to 1 the secondary diazocompound CF 3 CN 2 CH 3 ( 2 ) follows the normal A ‐ S E 2 mechanism of rate‐determining proton transfer.

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