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Elucidation of the Mechanism of the 1,6‐Cuprate Addition to Acceptor‐Substituted Enynes through 13 C Kinetic Isotope Effects: Experimental and Theoretical Studies
Author(s) -
Mori Seiji,
Uerdingen Marc,
Krause Norbert,
Morokuma Keiji
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200462976
Subject(s) - kinetic isotope effect , cuprate , chemistry , kinetic energy , acceptor , mechanism (biology) , substrate (aquarium) , isotope , alkyl , computational chemistry , photochemistry , materials science , organic chemistry , deuterium , physics , doping , nuclear physics , optoelectronics , quantum mechanics , condensed matter physics , oceanography , geology
A combination of experimental and theoretical studies of 13 C kinetic isotope effects have led to a comprehensive mechanistic picture of the 1,6‐cuprate addition to acceptor‐substituted enynes. In the rate‐determining step, the new bond is formed from the triple bond of the substrate to the incoming alkyl group (see scheme).
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