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Your search keyword '"Leonard A. Van Vliet"' showing total 2 results
Start Over Author "Leonard A. Van Vliet" Topic allylic rearrangement
2 results on '"Leonard A. Van Vliet"'

1. Intramolecular cyclization of (allylthio)sulfines via their vinylsulfenic acid tautomers

Author

Leonard A. Van Vliet, Paolo Zani, Bianca F. Bonini, René Ruinaard, Binne Zwanenburg, and Germana Mazzanti

Subjects
chemistry.chemical_classification, Reaction mechanism, Allylic rearrangement, Intramolecular reaction, Double bond, Stereochemistry, Organic Chemistry, Biochemistry, Tautomer, Medicinal chemistry, Sulfone, chemistry.chemical_compound, chemistry, Intramolecular force, Drug Discovery, Sulfenic acid
Abstract

Intramolecular cyclization of enethiolizable (allylthio)sulfines afford 2-alkylidene-1,3-dithiolane-1-oxides in good yields. The formation of these compounds can be explained by an initial tautomerization of the sulfine to vinyl sulfenic acid, followed by an intramolecular addition of the sulfenic acid to the allylic double bond. The stractures of the products were elucidated by means of 1H-and 13C-NMR spectroscopy as well as LIS effects, deuteriation experiments and an X-ray analysis.

Published
1992
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2. Intramolecular trapping reactions of vinylsulfenic acid tautomers of enethiolisable sulfines

Author

Leonard A. Van Vliet, René Ruinaard, Stefano Masiero, Binne Zwanenburg, Bianca F. Bonini, Esther van Helvoirt, and Germana Mazzanti

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, Allylic rearrangement, Thionyl chloride, Double bond, Chemistry, Intramolecular force, Substituent, Organic chemistry, Sulfenic acid, Trapping, Medicinal chemistry, Tautomer
Abstract

Thermal Intramolecular cyclisation of enethiolisable (allylsulfanyl)sulfines affords 2-alkylidene-1, 3-dithiolane 1-oxides in good yields. The formation of these compounds is explained by an initial tautomerisation of the sulfine to vinylsulfenic acid, followed by an Intramolecular addition of the sulfenic acid to the allylic double bond. Also, sulfines having an S-(prop-2-ynyl) substituent have been investigated and they similarly give 2-alkylidene-5-methylene-1, 3-dithiolane 1-oxides. The results obtained by using thionyl chloride to promote the reaction turned out to be highly dependent upon the structure of the starting sulfine.

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