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Tetrahedron

Stereochemical studies—79 synthesis and kinetic study on the retrodiene decomposition of norbornene-condensed 1, 3-oxazin-4-ones

G Stájer, LÓ Mód, AE Szabó, F Folöp, G Bernáth…

文献索引:Stajer, Geza; Mod, Laszlo; Szabo, Angela E.; Fueloep, Ferenc; Bernath, Gabor; Sohar, Pal Tetrahedron, 1984 , vol. 40, # 12 p. 2385 - 2393

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被引用次数: 31

摘要

The cis-cxo-amino acid c with norbornene skeleton was converted into 2-aryvl-cis-cxo-1, 3- oxazin-4-ones 5a-d. These compounds, similarly to the diendo isomers 1a-d studied by us earlier, undergo retrodiene decomposition under mild conditions to give 2-aryl-62-l, 3-oxazin- 6-ones (2 ad) in 50-60% yield. The ratio of the decomposition rate constants of the tricyclic diendo and diexo-1, 3-oxazin-4-ones, measured in toluene solution, is about 2.