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Stereochemistry of the hydrogenolysis of the benzyl oxygen bond. Application of racemic diastereoisomeric deuterium compounds

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Abstract

The stereochemistry of the hydrogenolysis of the benzyl oxygen bond in 3-methyl-2-phenyl-2-butanol has been established with the aid of racemicthreo-4-deuterio-3-methyl-2-phenyl-2-butanol (1) using PMR spectroscopy. Non-stereoselective hydrogen attack at C-2 of1 occurs using carbon-supported palladium as the catalyst and 90% acetic acid as the solvent at 30° and 1 atm.

Abstract

Стереохимия гидрогенолиза бензил-кислородной связи в 3-метил-2-фенил-2-бутаноле была определена с помощью трео-4-дейтеро-3-метил-2-фенил-2-бутанола (1), используя метод ПМР спектроскопии. В присутствии палладия на углеродном носителе, как катализатора, и 90%-ой уксусной кислоты, как растворителя, при температуре 30°C и давлеии 1 атм происходит нестереоселективая атака водорода на C-2 соединения 1.

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References

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  1. Laboratory of Organic Chemistry, Delft University of Technology, Julianalaan 136, 2208, Delft, The Netherlands

    A. P. G. Kieboom

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  1. A. P. G. Kieboom
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Kieboom, A.P.G. Stereochemistry of the hydrogenolysis of the benzyl oxygen bond. Application of racemic diastereoisomeric deuterium compounds. React Kinet Catal Lett 1, 433–434 (1974). https://doi.org/10.1007/BF02074475

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  • DOI: https://doi.org/10.1007/BF02074475

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