cap alpha. and. beta. deuterium isotope effects in the hydrolysis of naphthalene tetrahydro epoxides: rate-limiting hydrogen migration in the spontaneous hydrolysis of 6-methoxy-1,2,3,4-tetrahydronaphthalene oxide

Journal Article · Wed Aug 11 00:00:00 EDT 1982 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00380a028· OSTI ID:6713296

Gillilan, R E; Pohl, T M; Whalen, D L

Data are reported that indicate that 6-methoxy-1,2,3-tetrahydronaphthalene oxide undergoes a spontaneous reaction to yield mostly 6-methyoxy-2-tetralone. Hydrogen-migration is reported to be the rate determining step in the reaction. Reaction mechanisms involving a one-step reaction with a concurrent C-O bond cleavage and hydrogen migration or reversible C-O bond cleavage followed by the rate-limiting hydrogen migration are proposed, but no clear distinction between the schemes is made. (BLM)

• Research Organization: Univ. of Maryland Baltimore County, Baltimore
• OSTI ID: 6713296
• Journal Information: J. Am. Chem. Soc.; (United States), Vol. 104:16
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
DEUTERIUM
ISOTOPE EFFECTS
NAPHTHALENE
HYDROLYSIS
ORGANIC OXYGEN COMPOUNDS
CHEMICAL REACTION KINETICS
EXPERIMENTAL DATA
AROMATICS
CHEMICAL REACTIONS
CONDENSED AROMATICS
DATA
DECOMPOSITION
HYDROCARBONS
HYDROGEN ISOTOPES
INFORMATION
ISOTOPES
KINETICS
LIGHT NUCLEI
LYSIS
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
REACTION KINETICS
SOLVOLYSIS
STABLE ISOTOPES
400302* - Organic Chemistry- Isotope Effects- (-1987)