Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases p. 1213 - 1226 (1987)
Update date:2022-08-10
Topics:
Suzuki, Takashi
Tanaka, Katsumi
Toyoshima, Isamu
Okuhara, Toshio
Tanaka, Ken-ichi
Deuteration of buta-1,3-diene, 2-methylbuta-1,3-diene and penta-1,3-diene selectively yielded but-2-ene, 2-methylbut-2-ene and 1,4-<2H2>pent-2-ene on CdO and Co3O4, and but-1-ene, 2-methylbut-1-ene and 4,5-<2H2>pent-2-ene on Cr2O3, respectively.These results imply that the selectivity for 1,2- and 1,4-hydrogen addition is maintained in hydrogenation of conjugated dienes, i.e. 1,4-addition on CdO and Co3O4, and 1,2-addition on Cr2O3.The hydrogenation of buta-1,3-diene using a 1:1 mixture of H2 and D2 gave <2H2>but-1-ene in larger amounts than the <2H0>isomer on Cr2O3.An isotope effect smaller than unity was interpreted by prefential adsorption of D2 on the Cr2O3 surface.Formation of <2H1>butene was dominant in deuteration of buta-1,3-diene, indicating that residual hydrogen participates in the reaction; the amount corresponded to 7 times as much as that of chemisorbed hydrogen at room temperature.Co-isomerization of <2H0> and <2H8>but-1-ene yielded, selectively, <2H0>but-2-ene on CdO.Hydrogenation of buta-1,3-diene with a 1:1:1 mixture of H2, HD and D2 also gave <2H0>butene isomers selectively on CdO.These results infer that one intermediate species for hydrogenation of buta-1,3-diene is closely related to that for isomerization of butenes, and these reactions occur through a ?-allylic anion intermediate on CdO.
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