Deuteration of 4-t-butyl-1-cyclohexenyl methyl ether catalyzed by platinum metals: evidence for staggered. cap alpha beta. -diadsorbed intermediates

Journal Article · Thu May 01 00:00:00 EDT 1980 · J. Catal.; (United States)

DOI:https://doi.org/10.1016/0021-9517(80)90063-9· OSTI ID:6644447

Teratani, S; Takagi, Y; Tanaka, K; Muramatsu, Y

Deuteration of 4-t-butyl-1-cyclohexenyl methyl ether was carried out at 80/sup 0/C in cyclohexane under pressure. Over Ru, Rh, and Pd, the reaction products consisted almost entirely of the cis and trans mixtures of the corresponding saturated ethers (cis- and trans-4-t-butyl-1-cyclohexyl methyl ether), whereas over Os, Ir, and Pt, hydrogenolysis to t-butylcyclohexane was not negligible. The isomeric mixtures were separated and analyzed for isotopic distributions by mass spectrometry (MS) and for deuterium positions whthin each molecule by NMR spectroscopy. With most catalysts, the MS-determined isotopic distribution pattern for the cis ether was quite different from that of the trans ether. Also the NMR-based deuterium distributions were markedly different between these isomers. These dissimilarities can be best explained by assuming a few staggered ..cap alpha beta..-diadsorbed species as intermediates in enol ether hydrogenation. 2 figures, 4 tables.

• Research Organization: Inst. of Physical and Chemical Research, Saitama, Japan
• OSTI ID: 6644447
• Journal Information: J. Catal.; (United States), Vol. 63:1
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
CYCLOHEXANE
DEUTERATION
CATALYSTS
DEUTERIUM
ENOLS
HYDROGENATION
IRIDIUM
ISOMER SHIFT
MASS SPECTROSCOPY
MEDIUM TEMPERATURE
METHYL ETHER
NUCLEAR MAGNETIC RESONANCE
OSMIUM
PALLADIUM
PLATINUM
REACTION INTERMEDIATES
RHODIUM
RUTHENIUM
ALCOHOLS
ALKANES
CHEMICAL REACTIONS
CYCLOALKANES
ELEMENTS
ETHERS
HYDROCARBONS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
METALS
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PLATINUM METALS
REFRACTORY METALS
RESONANCE
SPECTROSCOPY
STABLE ISOTOPES
TRANSITION ELEMENTS
400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)