Intramolecular and intermolecular kinetic isotope effects (KIE) in the nitrosoarene ene reaction: Experimental evidence for reversible intermediate formation

…, O Krebs, M Orfanopoulos, M Stratakis…

Index: Adam, Waldemar; Krebs, Oliver; Orfanopoulos, Michael; Stratakis, Manolis Journal of Organic Chemistry, 2002 , vol. 67, # 24 p. 8395 - 8399

Full Text: HTML

Citation Number: 22

Abstract

The intramolecular and intermolecular kinetic isotope effects (KIE) have been determined for the nitrosoarene ene reaction with deuterium-stereolabeled 2, 3-dimethyl-2-butenes (TME). trans-TME-d 6 (k H/k D= 3.0) and gem-TME-d 6 (k H/k D= 4.0) show large intramolecular primary isotope effects. In contrast, the intramolecular competition in cis-TME-d 6 (k H/k D= 1.5) and the intermolecular competition for the TME-d 0/TME-d 12 pair (k H/k D= 1.98) ...

Related Articles:

Nickel (0)-catalyzed cross-coupling of alkyl arenesulfonates with aryl grignard reagents

[Cho, Chul-Hee; Yun, Hee-Sung; Park, Kwangyong Journal of Organic Chemistry, 2003 , vol. 68, # 8 p. 3017 - 3025]

Heterogeneous reactions with zinc. II. General synthesis of ketones from 1, 2-trisubstituted glycol monoesters and the mechanism of the serini reaction

[Ghera,E. Journal of Organic Chemistry, 1970 , vol. 35, p. 660 - 666]

An interesting rearrangement of unsaturated sulphonate and thiosulphonate esters

[Belletire, J. L.; Walley, D. R.; Bast, M. J. Synthetic Communications, 1982 , vol. 12, # 6 p. 469 - 476]

Kinetics of methanolysis and of sodium methoxide induced elimination from substituted benzyldimethylcarbinyl chlorides

[Bunnett,J.F.; Sridharan,S. Journal of Organic Chemistry, 1979 , vol. 44, # 9 p. 1458 - 1463]

Kinetics of methanolysis and of sodium methoxide induced elimination from substituted benzyldimethylcarbinyl chlorides

[Bunnett,J.F.; Sridharan,S. Journal of Organic Chemistry, 1979 , vol. 44, # 9 p. 1458 - 1463]

More Articles...