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Kinetic Resolution in the [2+2] Cycloaddition of Ketenes: An Experimental and Theoretical Study
Author(s) -
Rullière Pauline,
Carret Sébastien,
Milet Anne,
Poisson JeanFrançois
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405393
Subject(s) - cycloaddition , kinetic energy , kinetic resolution , olefin fiber , chemistry , computational chemistry , resolution (logic) , activation energy , organic chemistry , catalysis , computer science , physics , quantum mechanics , enantioselective synthesis , artificial intelligence
The kinetic resolution of Z and E olefins by [2+2] cycloaddition with ketenes allows the isolation of pure E olefin, as well as the synthesis of pure cis ‐cyclobutanones, starting from Z / E mixtures. A computational rationale for this kinetic difference is reported. The obtained difference of energy of activation matches with the experimental results.