Fragmentation of 1-alkyl derivatives of 5- and 7-nitro-2,1-benzisothiazoline 2,2-dioxides upon electron ionization

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Eur. J. Mass Spectrom. 3, 55 - 65 (1997)

Fragmentation of 1-alkyl derivatives of 5- and 7-nitro-2,1-benzisothiazoline 2,2-dioxides upon electron ionization

Witold Danikiewicz^* and Krzysztof Wojciechowski
Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland.

ABSTRACT:

Fragmentation patterns upon electron ionization of some 1-alkyl-5-nitro- and 1-alkyl-7-nitro-2,1-benzisothiazoline 2,2-dioxides are described. It is observed that the molecular ions of the 7-nitro isomers undergo rearrangement reactions resulting in the loss of a molecule of the appropriate carbonyl compound and, concurrently, an acyl radical. Mechanisms for these reactions, which can be assumed to be an example of the "ortho-effect", are proposed.

Keywords: EI fragmentation mechanisms, ortho-effect,2,1-benzisothiazoline 2,2-dioxide derivatives.

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