Mass spectra of heterocyclic compounds VI. 3,4‐dihydro‐1<i>H</i>‐2,3‐benzothiazine 2,2‐dioxides

Zinczuk, Juán; Bravo, Rodolfo D.; Orazi, Orfeo O.; Corral, Renée A.

doi:10.1002/oms.1210251006

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Electron impact‐induced fragmentation of 2,1‐benzisothiazoline 2,2‐dioxide

Danikiewicz

Wojciechowski

Fokkens

et al. 1993

Org. Mass Spectrom.

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The electron impact-induced fragmentation patterns of 2,l-benzisothiazoline 2,Mioxide nitro derivatives were studied. The rationalizations proposed for the fragmentations are supported by accurate mass measurements, daughter ion (mass analysed ion kinetic energy and B/E linked-scan), parent ion. and constant neutral loss spectra in metastable and collision-induced dissociation modes and deuterium labelling.

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Electron impact‐induced fragmentation of 2,1‐benzisothiazoline 2,2‐dioxide

Danikiewicz

Wojciechowski

Fokkens

et al. 1993

Org. Mass Spectrom.

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On the mechanisms of electron‐impact‐induced sulfur dioxide elimination from the molecular ions of 4‐nitro‐ and 6‐nitro‐2,1‐benzisothiazoline 2,2‐dioxide derivatives

Danikiewicz¹,

Wojciechowski²,

Fokkens³

et al. 1993

Rapid Comm Mass Spectrometry

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It is shown that metastably decomposing molecular ions of the title compounds eliminate sulfur dioxide via two reaction pathways provided that an a-hydrogen atom adjacent to the heterocyclic ring nitrogen atom is present. One of the channels leads to the initial formation of an o-azaxylylene ionic species and is associated with the narrow component of the accompanying composite metastable peak. The other channel involves a multistep pathway which eventually leads to the formation of an aldimine ionic species and which is associ!ted with the broad component of the accompanying composite metastable peak. Collision-induced dissociation and deuterium-labelling experiments have provided evidence that the initially generated o-azaxylylene ionic species, both as long-lived and as decomposing ions, have rearranged to the aldimine ionic species via a 1,s-shift of the ahydrogen atom adjacent to the heterocyclic ring nitrogen atom.

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