Premium
The cycloaddition of ethylene to butene‐2. I. Stereochemistry of the reaction
Author(s) -
Scacchi G.,
Richard C.,
Back M. H.
Publication year - 1977
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.550090402
Subject(s) - cyclobutanes , cyclobutane , chemistry , ethylene , cycloaddition , 2 butene , reaction rate constant , thermal decomposition , butene , photochemistry , decomposition , cis–trans isomerism , medicinal chemistry , stereochemistry , organic chemistry , kinetics , catalysis , ring (chemistry) , physics , quantum mechanics
The rate of the thermal cycloaddition of ethylene to cis and trans butene‐2 has been measured at 693°K and at pressures of about 12 atmospheres. The ratio of trans ‐ to cis ‐1,2‐dimethylcyclobutane from the reaction of trans ‐butene‐2 with ethylene was 5.1, obtained from the initial rates of formation of the products. Similarly, the ratio of cis ‐ to trans ‐1,2‐dimethyl‐cyclobutane from the reaction of cis ‐butene‐2 with ethylene was 2.8. The results show that the cycloaddition reactions are the reverse of the decomposition reactions of the dimethyl‐cyclobutanes and may be interpreted in terms of a biradical intermediate. Several ratios of rate constants have been measured as well as the rate constants for the reaction of the olefins to form the intermediate biradical.