Flash vacuum pyrolysis (F.V.P.) of 1,2,4-benzotriazine derivatives

Flash vacuum pyrolysis of 3-methylsulfanyl-1,2,4-benzotriazine N-oxide, 3-methylsulfanyl-1,2,4-benzotriazine, and 3-phenyl-1,2,4-benzotriazine are described. The N-oxide derivative underwent deoxygenation between 500 and 600°C, whereas at higher temperatures both methylsulfanyl compounds, besides yi...

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Bibliographic Details
Published inTetrahedron Vol. 59; no. 6; pp. 851 - 856
Main Authors Riedl, Zsuzsanna, Hajós, György, Peláez, Walter J, Gafarova, Ioulia T, Moyano, Elizabeth L, Yranzo, Gloria I
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 03.02.2003
Subjects
benzotriazines
flash vacuum pyrolysis
heterocycles
radicals
radicals
flash vacuum pyrolysis
heterocycles
benzotriazines
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Summary:Flash vacuum pyrolysis of 3-methylsulfanyl-1,2,4-benzotriazine N-oxide, 3-methylsulfanyl-1,2,4-benzotriazine, and 3-phenyl-1,2,4-benzotriazine are described. The N-oxide derivative underwent deoxygenation between 500 and 600°C, whereas at higher temperatures both methylsulfanyl compounds, besides yielding the same products, also gave benzimidazole formed by an independent mechanism. Transformation of these derivatives between 600 and 750°C led to formation of a complex reaction mixture indicating the radical nature of the processes. The phenyl substituted derivative was studied between 575 and 650°C and afforded benzonitrile and traces of biphenylene. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)01598-3