DOI: 10.1246/bcsj.56.780. Stereochemistry of the Palladium-catalyzed Hydrogenation of 3-Oxo-4-ene Steroids. V. A Kinetic Study in Basic and Acidic Media

Stereochemistry of the Palladium-catalyzed Hydrogenation of 3-Oxo-4-ene Steroids. V. A Kinetic Study in Basic and Acidic Media

10.1246/bcsj.56.780

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract Effects of the β-methyl group at C-10 and some oxygen functions (=O, OH, OAc) at C-11, C-17, and C-20 on the rates of hydrogenation of 3-oxo-4-ene steroids have been studied with palladium catalyst in pyridine or THF/HBr as solvent. In contrast to the hydrogenation in pyridine, the rate in THF/HBr was greatly depressed by the presence of 10β-methyl group. The reactivity of the steroids was enhanced by the oxygen functions, in particular, by 11, 17-dioxo group. The effects of the substituents are discussed from a mechanistic consideration based on the obtained results.

Bibliography

Nishimura, S., Momma, Y., Kawamura, H., & Shiota, M. (1983). Stereochemistry of the Palladium-catalyzed Hydrogenation of 3-Oxo-4-ene Steroids. V. A Kinetic Study in Basic and Acidic Media. Bulletin of the Chemical Society of Japan, 56(3), 780â783.

Authors 4

Shigeo Nishimura (first)
Yasuhiro Momma (additional)
Hideo Kawamura (additional)
Michio Shiota (additional)

References 11 Referenced 10

10.1021/jo01301a043
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10.1016/0040-4020(59)80008-9
10.1021/jo01256a066
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10.1021/jo00800a059
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{'key': '2024011801580603500_r10'}
{'key': '2024011801580603500_r11'}

Dates

Type	When
Created	19 years, 1 month ago (July 25, 2006, 9:14 p.m.)
Deposited	1 year, 7 months ago (Jan. 17, 2024, 8:58 p.m.)
Indexed	2 weeks ago (Aug. 23, 2025, 1:02 a.m.)
Issued	42 years, 6 months ago (March 1, 1983)
Published	42 years, 6 months ago (March 1, 1983)
Published Online	19 years, 2 months ago (June 27, 2006)
Published Print	42 years, 6 months ago (March 1, 1983)

Funders 0

None

BibTeX

@article{Nishimura_1983, title={Stereochemistry of the Palladium-catalyzed Hydrogenation of 3-Oxo-4-ene Steroids. V. A Kinetic Study in Basic and Acidic Media}, volume={56}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.56.780}, DOI={10.1246/bcsj.56.780}, number={3}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Nishimura, Shigeo and Momma, Yasuhiro and Kawamura, Hideo and Shiota, Michio}, year={1983}, month=mar, pages={780–783} }

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