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Reactivities of mixed organozinc and mixed organocopper reagents . Part 7. Comparison of the transfer rate of the same group in allylation of mixed and homo diorganozinc reagents
Author(s) -
Kalkan Melike,
Erdik Ender
Publication year - 2013
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3080
Subject(s) - chemistry , reagent , alkyl , leaving group , bromide , group (periodic table) , reaction rate , medicinal chemistry , kinetic energy , allyl bromide , inorganic chemistry , organic chemistry , catalysis , physics , quantum mechanics
A detailed direct kinetic study has been carried out to compare the reaction rate of transferable group, Ph in mixed phenylzinc reagents, RPhZn (R = n‐alkyl) and in homo diphenylzinc reagent, Ph 2 Zn in their reactions with allyl bromide in THF at 25–(−15) °C. Empirical rata law and activation parameters are consistent with a second‐order substitution reaction . The allylation rate of transferable group Ph in RPhZn (R = n‐alkyl) has been found higher than the rate of Ph group in Ph 2 Zn. A mechanism which accommodates the kinetic data and higher allylation rate of transferable group Ph in RPhZn than that in Ph 2 Zn is given. Copyright © 2013 John Wiley & Sons, Ltd.