The synthesis, X-ray structural analysis, and anomeric effect in trans-3,6-dimethoxy-1,2,4,5-tetroxane
作者:Chin-Yun Chiang、William Butler、Robert L. Kuczkowski
DOI:10.1039/c39880000465
日期:——
The ozonolysis of 1,2-dimethoxyethylene produces trans-3,6-dimethoxy-1,2,4,5-tetroxane which has a chair conformation with diaxial methoxy substituents and carbon–oxygen bond distances characteristic of anomeric and exo-anomeric interactions between the methoxy groups and the ring.
Ozonolyses of the 1-substituted methyl vinyl ethers 5, 8, and 16, bearing bulky substituents, and of the 2-substituted and 2,2-disubstituted methyl vinyl ethers 25 and 30, respectively, afforded the corresponding ozonides which have been isolated and characterized. In most cases, dry ozonolysis on polyethylene was advantageous over ozonolysis in solution. Ozonolysis of the 1,2,2-trisubstituted vinyl ether 34 gave no ozonide under either conditions.
Ozonolysis of 1,1-dimethoxyethene, 1,2-dimethoxyethene and vinyl acetate
作者:Brenda J. Wojciechowski、Chin Yun Chiang、Robert L. Kuczkowski