Cantrell recently reported' that U.V. irradiation 2,4-cyclooctadienone (1) in methanol or ether gave in low yield (6-10%) a dimer, m.p. 173-174'. The proposed head-to-head cin-atiti structure (as in 4) was based on spectral data, recovery of starting dimer after treatment with methanolic sodium meth
Mechanism of photochemical dimerization of 2,4-cyclooctadienone
β Scribed by G.L. Lange; E. Neidert
- Publisher
- Elsevier Science
- Year
- 1972
- Tongue
- French
- Weight
- 193 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
In our earlier work on the photochemistry of 2,6-cycloheptadienone (I), we had shown that the course of the reaction is markedly influenced by the nucleophilicity of the solvent .employed (1). Irradiation of I in methyl alcohol gives a monocyclic ether II as the major primary product. On the other h
Irradiation of 2,7-cyclooctadienone 1 produces cis,trans-2,7-cyclooctadienone 5 which has been characterized by low temperature, 13C NMR. Dienone 5 is in equilibrium with a zwitterionic oxyallyl species 6 via B, B bond formation. Zwitterion 6 forms cycloadducts with ethyl vinyl ether and 2-methoxyp