Interconversions, reactivities, and structures of isomeric hydrothiochromenes
2,4-Diphenyl-5,6,7,9-tetrahydrothiochromene was isomerized to 2,4-diphenyl-5,6-tetramethylene-4H-thiopyran in the presence of HCl and DCl. The relative thermodynamic stabilities of 2,4-diphenyl-5,6-tetramethylene-6H-thiopyran and the compound thus obtained were studied. The reactivities of the isomers of all three compounds in oxidation, disproportionation, and alkylation reactions are discussed. The structures of 2,4-diphenyl-5,6,7,9-tetrahydrothiochromene and 2,4-diphenyl-5,6-tetramethylene-4H-thiopyran were established by x-ray diffraction analysis.
KeywordsOxidation Organic Chemistry Alkylation Diffraction Analysis Disproportionation
Unable to display preview. Download preview PDF.
- 1.V. G. Kharchenko, S. K. Klimenko, V. I. Kleimenova, N. M. Kupranets, and A. R. Yakoveva, Khim. Geterotsikl. Soedin., No. 3, 73 (1971).Google Scholar
- 2.S. K. Klimenko and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 3, 85 (1971).Google Scholar
- 3.S. K. Klimenko, M. N. Berezhnaya, T. V. Stolbova, I. Ya. Evtushenko, and V. G. Kharchenko, Zh. Org. Khim., 11, 2173 (1975).Google Scholar
- 4.S. K. Klimenko, T. V. Stolbova, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 10, 1338 (1981).Google Scholar
- 5.E. T. Ostensen and M. M. Mishrikey, Acta Chem. Scand., B, 30, 635 (1976).Google Scholar
- 6.E. T. Ostensen, A. A. Abdallah, S. H. Scaare, and M. M. Mishrikey, Acta Chem. Scand., B, 31 496 (1977).Google Scholar
- 7.I. C. P. Shwarz, Chem. Commun., 6, 505 (1973).Google Scholar
- 8.A. Smith, R. Kalish, and E. I. Smuthy, Acta Crystallogr., B, 28, 3494 (1972).Google Scholar
- 9.Tables of Interatomic Distances and Configurations in Molecules and Ions, Supplement, L. E. Sutton, ed., 1958–1959, London (1968).Google Scholar