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Gas-phase thermolysis of sulfur compounds. Part III: n-butyl 2-propenyl sulfide

✍ Scribed by Gonzalo Martin; Alberto Drayer; Marcos Ropero; Miguel E. Alonso

Publisher
John Wiley and Sons
Year
1982
Tongue
English
Weight
463 KB
Volume
14
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The pyrolysis of n‐butyl 2‐propenyl sulfide has been investigated in a static system in the initial pressure range of 50–350 torr. The reaction was found to be homogeneous and first order. The rate coefficients are given by the Arrhenius equation
between 262 and 293°C. The rate of the reaction remains unchanged in the presence of cyclohexene as radical inhibitor. The main reaction products were propene and a trimer of n‐butyl thioaldehyde. The results are interpreted in terms of a molecular mechanism involving a cyclic six‐centered transition state. This mechanism is supported by the pyrolysis of 1,1‐dideutero‐n‐butyl 2‐propenyl sulfide at 281°C. The kinetic deuterium isotope effect had a value of 2.7 ± 0.2. Nuclear magnetic resonance and mass spectroscopic analysis of the reaction products showed the deuterium to be distributed as expected from the proposed reaction mechanism.

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