The Reactions of Deuterium-Labeled 1-ButanethioIs (1, l-d2-, 2, 2-d2 and 4,4,4-d3-l-Butanethiol) with H and D atom

Tohru Kamo, Jie Tang, Muneyoshi Yamada

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Abstract

The reaction of d0-, 1, l-d2-, 2,2-d2- and 4,4,4-d3-l-butanethiols with H and D atom have been investigated at room temperature, under 530 and 2660 Pa, using a conventional discharge flow apparatus. Butane and 1-butene were produced mainly. Small amounts of ethylene, propylene, x propane, and ethane were also detected (Table 1). Relative amount of butane increased slightly as conversion increased, while that of 1-butene decreased (Figs. 1 and 2). The decrease of 1-butene could be accounted for by secondary reactions with H/D atom (Table 2). The numer of D atoms in unreacted thiols was unaffected by the reaction. The number of D atoms in butane remained unchanged with that in the substrate thiols when the reaction was carried out with H atom, but it increased precisely by one when reacted with D atom (Table 3). The number of D atoms in 1-butene remained unchanged in the reaction of d0-, 1, l-d2- and 4,4,4-d3-l-butanethiols, irrespective of the reaction partner, H or D atom. But one D atom was lost in 1-butene from 2,2-d2-l-butanethiol (Table 4). Deuterium distribution in butane and 1-butene can be, explained by abstraction and addition reaction between butyl radical and H/D atom. However, the amount of 1-butene can not be explained only by these reactions, since the abstraction/addition ratio is estimated to be small, ca. 0.05 (Table 5). The D atom distribution and relative amount of 1-butene were taken in support for concomitant elimination of mercapto group and hydrogen at the second position from the substrate thiols. From these results, the following scheme is proposed.

Original languageEnglish
Pages (from-to)688-695
Number of pages8
JournalNIPPON KAGAKU KAISHI
Volume1987
Issue number4
DOIs
Publication statusPublished - 1987
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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