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Ene reactions of olefins. I. The addition of ethylene to 2-butene and the decomposition of 3-methylpentene-1

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

Publisher
John Wiley and Sons
Year
1978
Tongue
English
Weight
639 KB
Volume
10
Category
Article
ISSN
0538-8066

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✦ Synopsis

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 cyclopentene was formed from radical processes while 3‐methylpentene‐1 was formed by the molecular “ene¨︂” addition of ethylene to butene‐2 through a six‐center transition state. The following rate constants were obtained:
equation image
The pyrolysis of 3‐methylpentene‐1 has been studied over the same temperature range and for initial pressures of 20–100 torr. Kinetic evidence showed that the products ethylene and butenes were formed in both radical and molecular processes. Estimates of the rate constant k~−1__t__~ and k~−1__c__~ were, however, in reasonable agreement with the measurements of k~1__t__~ and k~1__c__~. The mechanism of the ene reaction is discussed, and it is concluded that the transition state does not involve the formation of a biradical.

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