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Excluding cyclopentadienone as an intermediate in the thermolysis of (3) we feel that the difference in thermolytic fragmentation of 0-and p-benzoquinone can be explained by assuming that primarily a cyclopropanone-type intermediate is formed in the case of p-benzoquinone. Bicyclo-[2.1.0]pent-4-en-2-one ( 4 ) is likely to give a C,H, species (butadiene diradical, cyclobutadiene or tetrahedrane) ultimately leading to vinylacetylene, since it is known"] that cyclopropanones lose CO under relatively mild conditions. 1,2-and 1,4-Naphthoquinone show a similar difference in their thermal fragmentation patterns['?
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the reaction leads to ring opening. We have succeeded in preparing (2) by direct reaction of 4-amino-5-dimethoxymethylpyrimidine ( 1 ) I21 with s-triazine. Compound (2) is very sensitive toward water. Its structure has been proved by elemental analysis and by IR and N M R spectroscopy. The N M R sig
The whole is then left standing for 1 --2 days at O O C . Alkaline alcoholic solutions vacuum sublimation of the residue left after evaporation of the ether from the extract. Compound (2c) is isolated as its picrate, made by boiling the (3-dicarbonyl compound with picric acid in ethanol. COOCrH5 COO