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The cycloaddition of ethylene to butene-2. I. Stereochemistry of the reaction

✍ Scribed by G. Scacchi; C. Richard; M. H. Back

Publisher
John Wiley and Sons
Year
1977
Tongue
English
Weight
549 KB
Volume
9
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

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.

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The cycloaddition of ethylene to butene-
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✍ G. Scacchi; M. H. Back 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 English ⚖ 436 KB

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✍ C. Richard; G. Scacchi; M. H. Back 📂 Article 📅 1978 🏛 John Wiley and Sons 🌐 English ⚖ 639 KB

## Abstract The pyrolysis of ethylene–butene‐2 mixtures has been studied in a static system over the temperature range of 689°‐754°k and for initial pressures of each olefin of 20–200 torr. The two main addition products were cyclopentene and 3‐methylpentene‐1. Kinetic evidence indicated that cyclo