1-methoxy-3,5-diaryl-2-oxabicyclo[4.4.0]dec-3-enes from “semicyclic” 1,5-diketones
- 26 Downloads
It was established that “semicyclic” 1,5-diketones are capable of reacting with methanol by the catalytic action of hydrogen chloride and are capable of forming 1-methoxy-3,5-diaryl-2-oxabicyclo [4.4.0]dec-3-enes — cyclic acetals that include an alkoxydihydropyran ring. In addition, 2,4-darylbicycle[3.3.1]non-2-en-9-ones, which are formed from 1,3-diaryl-3-(2-oxocyclohexyl)propan-1-ones by an intramolecular condensation of the erotonic type, are detected as side products. The possible mechanism of the reaction of 1,3-diaryl-3-(2-oxocyclohexyl)propan-1-ones with methanol in the presence of hydrogen chloride is discussed.
KeywordsHydrogen Acetal Chloride Methanol Organic Chemistry
Unable to display preview. Download preview PDF.
- 1.H. Stobbe, J. Prakt. Chem., 86, 209, 218 (1912).Google Scholar
- 2.C. F. Allen and H. R. Sallans, Can. J. Res., 9, 574 (1933).Google Scholar
- 3.W. Dilthey, J. Prakt. Chem., 94, 53 (1916).Google Scholar
- 4.W. Dilthey, J. Prakt. Chem., 95, 107 (1917).Google Scholar
- 5.V. G. Kharchenko, N. M. Kupranets, S. K. Klimenko, and M. N. Berezhnaya, Zh. Org. Khim., 8, 390 (1972).Google Scholar
- 6.I. Ya. Evtushenko, S. K. Klimenko, V. G. Kharchenko, and B. I. Ionin, Zh. Org. Khim., 12, 1807 (1976).Google Scholar
- 7.O. H. Wheeler and J. L. Mateos, Anal. Chem., 29, No. 1, 538 (1957).Google Scholar
- 8.O. H. Wheeler, J. Am. Chem. Soc., 79, 4191 (1957).Google Scholar
- 9.V. I. Vysotskii and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 3, 383 (1976).Google Scholar
- 10.E. D. Bergmann and A. Kaluszyner, Rec. Trav. Chim., 78, 337 (1959).Google Scholar
- 11.S. V. Soboleva, O. D. D'yachenko, L. O. Atovmyan, V. G. Kharchenko, and S. K. Klimenko, Zh. Strukt. Khim., 19, 499 (1978).Google Scholar