Benz-1,2,3-oxathiazin-4(3F)-one-2,2-dioxides, a process for their preparation and their use as electrophilic fluorinating agents

US5525729A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Ivan Cabrera · Dreieich, DE
• Wolfgang Appel · Kelkheim, DE

Key dates

• Filing date: Mar 13, 1995
• Grant date: Jun 11, 1996
• Expiry date: Mar 13, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B39/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to compounds of the formula (I) ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are, independently of one another, hydrogen, CF.sub.3, NO.sub.2, CN, halogen, --S(NSO.sub.2 CF.sub.3)CF.sub.3, (C.sub.1 -C.sub.4)-alkyl, phenyl, SO.sub.2 R.sup.5, COOR.sup.5, NR.sub.2.sup.5, where R.sup.5 is (C.sub.1 -C.sub.4)-alkyl, which can also be fluorinated, or phenyl, or R.sup.1 and R.sup.2, R.sup.2 and R.sup.3 or R.sup.3 and R.sup.4 together form an aliphatic or aromatic ring which can also contain an oxygen, sulfur or nitrogen atom. The invention further provides a process for preparing the compounds of the formula (I), which comprises reacting compounds of the formula (II) ##STR2## where R.sup.1 to R.sup.4 are as defined above and X is hydrogen or an alkali metal, with elemental fluorine in the presence of an inert solvent and, if desired, an alkali metal fluoride at low temperatures. The invention further provides for the use of the compounds of the formula (I) for the fluorination of compounds having carbanion character.