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Kinetics and Mechanism of 1,3‐Dipolar Cycloadditions
Author(s) -
Huisgen R.
Publication year - 1963
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196306331
Subject(s) - chemistry , stereoselectivity , mechanism (biology) , kinetics , dipole , concerted reaction , reaction rate constant , computational chemistry , solvent , atomic orbital , orientation (vector space) , solvent effects , reaction mechanism , molecular orbital , molecule , chemical physics , stereochemistry , catalysis , organic chemistry , physics , quantum mechanics , mathematics , geometry , electron
Criteria for the mechanism of 1,3‐dipolar cycloadditions which lead to 5‐membered rings are provided by the stereoselectivity observed with cis‐trans isomeric dipolarophiles, by the effect of solvent and substituents on the rate constants, by the activation parameters, and by orientation phenomena. A concerted addition, which can also be described in terms of molecular orbitals and in which the two new σ‐bonds are formed simultaneously, although not necessarily at equal rates, offers the best explanation of the experimental facts.