- Facile direct conversion of aminoheterocycles to fluoro-heterocycles using t-butylthionitrite or t-butylthionitrate with sodium tetrafluoroborate
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Amino-nucleic acids and amino-heterocycles reacted readily with t-butylthionitrite or t-butylthionitrate in the presence of anhydrous sodium tetrafluoroborate in neutral and aprotic media to afford the corresponding fluoro-nucleic acids and fluoroheterocycles respectively in good yields.
- Kim, Yong Hae,Lee, Chun Ho,Chang, Ki Young
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- ORGANIC SYNTHESIS USING ORGANOSULFUR-NITRITES AND -NITRATES
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Thionitrites or thionitrates have been considered to be unstable.However, bulky groups' thio-NOn such as t-butylthio-nitrites and -nitrates have been readily synthesized and found to be stable enough for the use of the useful organic syntheses as an excellent nitrosation and diazotization reagents under mild conditions.Direct conversion of amines to the corresponding halides in the presence of copper halides (II), fluorination of heterocyclic amines in the presence of sodium tetrafluoroborate, α- oximation of methylene groups in ketones, facile cleavage of C=N bond to ketones, and desulfurization of thioacetals and thioketals, and other useful organic syntheses are described.
- Kim, Yong Hae
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p. 249 - 260
(2007/10/02)
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