Transformation of organic compounds in the presence of metal complexes. II. Reduction of alkyl-substituted cyclohexanones via hydrogen-transfer reactions catalysed by rhodium(I) complexes

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Abstract

Catalyst systems prepared in situ from bidentate phosphines (Ph2P(CH2)nPPh2, where n = 1-4) and from [Rh(COD)Cl]2 proved to be active in the transfer hydrogenation of alkylcyclohexanones (alkyl = 2-Me, 4-Me, 4-t-Bu, cis-2,6-Me2). With the exception of 4-methylcyclohexanone, which gave a cis/trans-cyclohexanol ratio of ∼ 1, mainly cis alcohols were formed, their amounts increasing in proportion to the value of n. No reduction occurred in the case of 2-t-butyl- and 2,6-di-t-butyl-cyclohexanones.

Original languageEnglish
Pages (from-to)439-441
Number of pages3
JournalJournal of Organometallic Chemistry
Volume277
Issue number3
DOIs
Publication statusPublished - Dec 18 1984

Fingerprint

Cyclohexanones
Cyclohexanols
Phosphines
Rhodium
Hydrogenation
crack opening displacement
Coordination Complexes
Metal complexes
rhodium
organic compounds
Organic compounds
phosphines
hydrogenation
Hydrogen
proportion
alcohols
Alcohols
catalysts
Catalysts
hydrogen

ASJC Scopus subject areas

  • Biochemistry
  • Chemical Engineering (miscellaneous)
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Science (miscellaneous)
  • Materials Chemistry

Cite this

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title = "Transformation of organic compounds in the presence of metal complexes. II. Reduction of alkyl-substituted cyclohexanones via hydrogen-transfer reactions catalysed by rhodium(I) complexes",
abstract = "Catalyst systems prepared in situ from bidentate phosphines (Ph2P(CH2)nPPh2, where n = 1-4) and from [Rh(COD)Cl]2 proved to be active in the transfer hydrogenation of alkylcyclohexanones (alkyl = 2-Me, 4-Me, 4-t-Bu, cis-2,6-Me2). With the exception of 4-methylcyclohexanone, which gave a cis/trans-cyclohexanol ratio of ∼ 1, mainly cis alcohols were formed, their amounts increasing in proportion to the value of n. No reduction occurred in the case of 2-t-butyl- and 2,6-di-t-butyl-cyclohexanones.",
author = "K. Felf{\"o}ldi and I. Kapocsi and M. Bart{\'o}k",
year = "1984",
month = "12",
day = "18",
doi = "10.1016/0022-328X(84)80729-9",
language = "English",
volume = "277",
pages = "439--441",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",
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TY - JOUR

T1 - Transformation of organic compounds in the presence of metal complexes. II. Reduction of alkyl-substituted cyclohexanones via hydrogen-transfer reactions catalysed by rhodium(I) complexes

AU - Felföldi, K.

AU - Kapocsi, I.

AU - Bartók, M.

PY - 1984/12/18

Y1 - 1984/12/18

N2 - Catalyst systems prepared in situ from bidentate phosphines (Ph2P(CH2)nPPh2, where n = 1-4) and from [Rh(COD)Cl]2 proved to be active in the transfer hydrogenation of alkylcyclohexanones (alkyl = 2-Me, 4-Me, 4-t-Bu, cis-2,6-Me2). With the exception of 4-methylcyclohexanone, which gave a cis/trans-cyclohexanol ratio of ∼ 1, mainly cis alcohols were formed, their amounts increasing in proportion to the value of n. No reduction occurred in the case of 2-t-butyl- and 2,6-di-t-butyl-cyclohexanones.

AB - Catalyst systems prepared in situ from bidentate phosphines (Ph2P(CH2)nPPh2, where n = 1-4) and from [Rh(COD)Cl]2 proved to be active in the transfer hydrogenation of alkylcyclohexanones (alkyl = 2-Me, 4-Me, 4-t-Bu, cis-2,6-Me2). With the exception of 4-methylcyclohexanone, which gave a cis/trans-cyclohexanol ratio of ∼ 1, mainly cis alcohols were formed, their amounts increasing in proportion to the value of n. No reduction occurred in the case of 2-t-butyl- and 2,6-di-t-butyl-cyclohexanones.

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