Temperature, solvent, and substituent effects on the singlet oxidations of allylic phenyl sulfoxides, sulfones, and sulfides

Journal Article · Wed Oct 11 00:00:00 EDT 1989 · Journal of the American Chemical Society; (USA)

DOI:https://doi.org/10.1021/ja00203a023· OSTI ID:6730703

Clennan, E L; Chen, Xiangning ^[1]

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1. Univ. of Wyoming, Laramie (USA)

The reactions of singlet oxygen with a series of allylic sulfoxides, sulfones, and sulfides have been examined as a function of extent of reaction, temperature, and solvent. Hydroperoxy groups but not alkyl, hydrogen, or hydroxyl on chiral carbons {beta} to sulfide sulfur induce diastereoselective sulfoxide formations. Evidence is presented that suggests that the oxidation at sulfur occurs with anchimeric assistance from the hydroperoxy group via a favorable sulfurane-like transition state.

• OSTI ID: 6730703
• Journal Information: Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 111:21; ISSN 0002-7863; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
CALCULATION METHODS
CHALCOGENIDES
CHEMICAL REACTIONS
CHEMISTRY
DATA
DATA ANALYSIS
EXPERIMENTAL DATA
INFORMATION
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXIDATION
PHOTOCHEMISTRY
SOLVENT PROPERTIES
SULFIDES
SULFONES
SULFOXIDES
SULFUR COMPOUNDS
TEMPERATURE EFFECTS