The Mechanism Study of Free Radical S H 2′ Reactions by Leaving Group Effect and Secondary α‐Deuterium Kinetic Isotope Effect | Zendy

Wu YuhWern | Zendy; Huang ShuHui | Zendy; Tseng TeongFuh | Zendy; Yang JyhFerng | Zendy

Premium

The Mechanism Study of Free Radical S H 2′ Reactions by Leaving Group Effect and Secondary α‐Deuterium Kinetic Isotope Effect

Author(s) -

Wu YuhWern,

Huang ShuHui,

Tseng TeongFuh,

Yang JyhFerng

Publication year - 2004

Publication title -

journal of the chinese chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.329

H-Index - 45

eISSN - 2192-6549

pISSN - 0009-4536

DOI - 10.1002/jccs.200400150

Subject(s) - chemistry , kinetic isotope effect , deuterium , leaving group , allylic rearrangement , chloride , photochemistry , elimination reaction , kinetic energy , catalysis , medicinal chemistry , organic chemistry , physics , quantum mechanics

The reactions of free radical addition to allylic compounds are believed to proceed the S H 2′ mechanism. It is not clear whether the S H 2′ mechanism is concerted or stepwise. The leaving group effects and the secondary α‐deuterium kinetic isotope effects in free radical S H 2′ reactions have been determined. The leaving group effect, k Br /k Cl , is from 1.88 to 14.3. The secondary α‐deuterium kinetic isotope effects, k H /k D , are 1.20 for 2‐methylallyl chloride and 1,1‐d 2 ‐2‐methylallyl chloride and 1.22 for allyl chloride and 1,1‐d 2 ‐allyl chloride. The free radical S H 2′ reactions seem to favor the concerted mechanism.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research