Deuterium isotope effects upon solvolyses of alkyl sulfonates in dimethyl sulfoxide
It was demonstrated that dimethyl sulfoxide is a useful complement to more commonly used solvents in the study of solvolysis reactions. Products of DMSO solvolysis have been characterized using deuterium magnetic resonance (DMR) spectrometry. Alpha and beta deuterium isotope effects were determined in the second part for solvolyses of pinacolyl sulfonates in solvents with a wide range of ionizing power and nucleophilicity. Solvolyses of pinacolyl perflate in DMSO yield 5-10% direct unrearranged substitution product. The solvolysis mechanism of cyclooctyl sulfonates was examined. Delta 97 T values for ethanol:TFE rate correlations were found to vary with leaving group, and alkyl group was examined.
- Research Organization:
- Indiana Univ., Bloomington (USA)
- OSTI ID:
- 6950180
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400202* -- Isotope Effects
Isotope Exchange
& Isotope Separation
ALKANES
CHEMICAL REACTIONS
DECOMPOSITION
DEUTERIUM
DMSO
HYDROCARBONS
HYDROGEN ISOTOPES
ISOTOPE EFFECTS
ISOTOPES
LIGHT NUCLEI
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
SOLVOLYSIS
STABLE ISOTOPES
SULFONATES
SULFOXIDES