By Graham Sandford (auth.), Jernej Iskra (eds.)
G. Sandford: Perfluoroheteroaromatic Chemistry: Multifunctional structures from Perfluorinated Heterocycles through Nucleophilic fragrant Substitution Processes.- A. A. Gakh: Monofluorinated Heterocycles.- R. Dembinski ∙ Y. Li ∙ D. Gundapuneni ∙ A. Decker: Synthesis of beta-Halofurans.- Y. Shermolovich ∙ S. Pazenok: Synthesis of halogenated five- and six-membered sulfur- and Sulfur, Nitrogen Containing Heterocycles.- S. Minakata ∙ Y. Takeda ∙ J. Hayakawa: Heterocyclic Reagents Containing Nitrogen-Halogen Bond: contemporary Applications.- Michael Schnürch: fresh development at the Halogen Dance response on Heterocycles.- T. Kosjek ∙ E. Heath: Halogenated Heterocycles as Pharmaceuticals.- E. Heath ∙ T. Kosjek: assets, prevalence and destiny of Halogenated Heterocyclic prescription drugs within the Environment.- J. Iskra: eco-friendly tools in Halogenation of Heterocycles.
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Extra info for Halogenated Heterocycles: Synthesis, Application and Environment
Example text
3 Four-Membered Monofluoroheterocycles . . . . . . . . . . . . . . . . . . . . . . . . . . 4 Five-Membered Monofluoroheterocycles . . . . . . . . . . . . . . . . . . . . . . . . . . 5 Six-Membered Monofluoroheterocycles . . . . . . . . . . . . . . . . . . . . . . . . . . . 6 Conclusions: The “Wish List” . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . References .
A. A. 2] octane bis-tetrafluoroborate Tetrabutylammonium fluoride Tetramethylammonium fluoride 1 Introduction Ring-fluorinated heterocycles containing only one fluorine atom (monofluorinated heterocycles) constitute an important family of organic compounds with a wide array of applications ranging from drugs to multi-ton industrial intermediates [1, 2]. Although the first representatives of monofluorinated heterocycles, including 2fluoropyridine [3], were synthesized almost 100 years ago, major developments in this field were made during the last two decades.
R1 O (C6H5SO2)2NF N N R R1 F O R2 R R2 17d Scheme 13 Stereoselective electrophilic fluorination of b-lactams Similar to 2-fluoroazetidine (16) and 3-fluoroazetidine (17), derivatives of 3-fluorooxetane (19) are better known and more studied than 2-fluorooxetane (18). Parent 3-fluorooxetane (19) can be easily prepared from 3-oxetyl tosy1ate and KF (Scheme 14) [20]. A. Gakh F OTs OH TsCl KF O O O 19 Scheme 14 Synthesis of 3-fluorooxetane (19) Alternatively, 3-oxetanols can be directly converted to 3-fluorooxetanes 19a using DAST as a fluorinating agent (Scheme 15).