PMR spectra and structure of the open form of spironaphthooxazine
The PMR spectra of the closed forms of spironaphthopyran and spironaphthooxazine were interpreted. The PMR spectra of the photoinduced forms of these compounds were obtained for the first time.
The open form of spironaphthooxazine in nonpolar solvents was found to have the quinoid structure of one of the trans isomers, while there is a shift in the equilibrium toward the bipolar structure in polar solvents.
KeywordsClosed Form Polar Solvent Trans Isomer Open Form Nonpolar Solvent
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- 1.V. S. Marevtsev, L. S. Kol'tsova, A. V. Lyubimov, and M. I. Cherkashin, Izv. Akad. Nauk SSSR, Ser. Khim., 2259 (1988).Google Scholar
- 2.N. Y. S. Chu, Can. J. Chem.,61, 300 (1983).Google Scholar
- 3.E. D. Bergman, A. Weizmann, and E. Fischer, J. Am. Chem. Soc.,72, 5009 (1950).Google Scholar
- 4.V. S. Marevtsev, N. L. Zaichenko, V. D. Ermakoa, et. al., Izv. Akad. Nauk SSSR, Ser. Khim., 2272 (1980).Google Scholar
- 5.B. I. Ionin and B. A. Ershov, NMR Spectroscopy in Organic Chemistry [in Russian], Khimiya, Leningrad (1967), p. 237.Google Scholar
- 6.H. Guenther, NMR Spectroscopy: An Introduction, Wiley, New York (1980).Google Scholar
- 7.A. J. Gordon and R. A. Ford, Chemist's Companion, Wiley, New York (1973).Google Scholar
- 8.W. Brügel, Nuclear Magnetic Resonance Spectra and Chemical Structure, Vol. 1, Academic Press, New York-London (1967), pp. 128–133.Google Scholar
- 9.A. I. Kiprianov, Usp. Khim.,29, 1336 (1960).Google Scholar
- 10.K. Tabei and E. J. Saitov, Bull. Chem. Soc. Jpn.,42, 1440 (1969).Google Scholar
- 11.R. Heiligman-Rim, Y. Hirshberg, and E. Fischer, J. Phys. Chem.,66, 2465 (1962).Google Scholar
- 12.C. Reichardt, Solvent Effects in Organic Chemistry, Verlag Chemie, Weinheim (1979).Google Scholar