Elemental fluorine. Part 5. Reactions of 1,3-dithiolanes and thioglycosides with fluorine–iodine mixtures
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 16,p. 1941-1944
- https://doi.org/10.1039/p19960001941
Abstract
1,3-Dithiolanes, prepared from diaryl ketones, react with elemental fluorine–iodine mixtures to give the corresponding difluoromethylene derivatives. Under the same conditions, thioglycosides give glycosyl fluorides in good yields. Reaction of 1,3-dithiolanes with fluorine in aqueous acetonitrile provides a remarkably mild method for efficient deprotection to the parent ketone.Keywords
This publication has 30 references indexed in Scilit:
- Elemental fluorine. Part 4. Use of elemental fluorine for the halogenation of aromaticsJournal of the Chemical Society, Perkin Transactions 1, 1996
- The conversion of diaryl-1,3-dithiolanes into gem-difluoromethylene compounds by a combination of elemental fluorine and iodineJournal of the Chemical Society, Chemical Communications, 1995
- Synthesis of chiral and bioactive fluoroorganic compoundsTetrahedron, 1993
- Recent advances in the selective formation of the carbon-fluorine bondChemical Reviews, 1992
- A Facile Synthesis of Difluoromethylene Compounds by Oxidative Fluorodesulfurization of Dithioacetals Using Tetrabutylammonium Dihydrogentrifluoride andN-Halo CompoundsSynlett, 1991
- A novel transformation of a carbonyl to a CF2 groupJournal of the American Chemical Society, 1987
- Tetrahedron report number 221Tetrahedron, 1987
- Gem-Difluoro compounds: a convenient preparation from ketones and aldehydes by halogen fluoride treatment of 1,3-dithiolanesThe Journal of Organic Chemistry, 1986
- Geminal fluorination of diazo compoundsThe Journal of Organic Chemistry, 1981
- Methods of Fluorination in Organic ChemistryAngewandte Chemie International Edition in English, 1981