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1 Bulletin of the Polish Academy of Sciences. Chemistry

1 2002

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Reaction of acetylenic gama-glycols. XXXVII. Dehydroxylation and decarbonylation processes in MS-spectra of sym. aromatic diols without and with halogen substituents in para position of phenyl

Jasiobędzki W., Olejnik M.

Bulletin of the Polish Academy of Sciences. Chemistry

2002

Vol. 50, No. 3

323-334

The electron ionization-induced fragmentation patterns of five diols (with H, F, Cl, Br, I substituents in para positions of phenyls) have been studied, especially the title processes. Alternation of dehydroxylation and decarbonylation processes has been found. The elimination of CO causes a rearrangement of the neighbouring aryl and H. The formation of cumulene ions is possible from M(+*)-H(2)O and M(+*)-H(2)O, X* ions. It has been shown that the acetylenic bond has the ability to hold Ph*", PhX* (X=halogen), CeH4, H. The halogen (type), in comparison with the unsubstituted diol, introduces quantitative and not qualitative changes. With a decrease in the induction effect of the halogen, the relative intensity (%) of fragment ions increases, especially of those having small m/z values.