Oxathiazinone Dioxides

These compounds (Formula 8.15) belong to a class of sweeteners with an AH/B-system corresponding to that of saccharin. Based on their properties and present toxicological data, they are suitable for use. The sweetening strength depends on substituents and R and is /ac,g(10) = 200 for acesulfame K (Table 8.9). 

The ADI value stipulated for the potassium salt of acesulfame is 0-9 mg/kg of body weight. 

Oxathiazinone dioxides are obtained from fluo-rosulfonyl isocyanate and alkynes, or from com- 

The sweetness of acesulfame is perceived quickly and this substance is practically stable in foods under the common processing and storage conditions. It is used in a large number of different products. 

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Structurally related to saccharin are the oxathiazinone dioxides (104). Clauss and coworkers synthesized a series of these compounds, and demonstrated that they possess intense sweetness. Acesulfame-K, the potassium salt of 3,4-dihydro-6-methyl-l,2,3-oxathiazin-4-one 2,2-dioxide (104) has a sweetness intensity 130 times that of sucrose. 

Oxathiazinone dioxides have been used for the synthesis of a new type of heterocyclic N — F reagent 4, which are obtained by direct fluorination of salts of the oxathiazinone dioxide derivatives 3 with a mixture of 5% fluorine in nitrogen at low temperatures.136 137 Isolation of the pure compound 4a or 4b is generally rather difficult and the material is not stable in air at room temperature. In contrast, 3-fluoro-l,2,3-benzoxathiazin-4(3//)-one 2,2-dioxide (4c) is a colorless, thermally stable solid with a melting point of 61 "C.137... 

Table 8.9. Sweetness of some oxathiazinone dioxides (Na-salts) (Formula 8.15)...

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