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

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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) ...