Acylthioketene-thioacylketene-thiet-2-one rearrangements

被引：19

作者：

Ammann, JR

Flammang, R

Wong, MW

Wentrup, C ^{[1
]}

机构：

[1] Univ Queensland, Dept Chem, Brisbane, Qld 4072, Australia

[2] Natl Univ Singapore, Dept Chem, Singapore 119260, Singapore

[3] Univ Mons, Organ Chem Lab, B-7000 Mons, Belgium

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 09期

关键词：

D O I：

10.1021/jo991776p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Flash vacuum thermolysis (FVT) of 6-aryl-1,3-dioxine-4-thiones 9 leads to the formation of acylthioketenes 10, which are characterized by Ar matrix IR spectroscopy as well as on-line tandem mass spectrometry. The thioketenes 10 undergo a 1,3-shift of the aryl group to generate thioacylketenes II. Ketenes 11 cyclize to 3-aryl-thiet-2-ones 12, which are also characterized by matrix IR spectroscopy and tandem mass spectrometry. The thiet-2-ones 12 undergo two kinds of reaction under the FVT conditions: (i) cheletropic CO extrusion with formation of arylthioketenes 13. and (ii) cycloreversion to COS and arylacetylene.

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页码：2706 / 2710

页数：5

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