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First investigations show that the spiro compounds obtained have photochromic properties: O. Brede and T. Zimmermann, unpublished results.
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note
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A careful analysis of the crude products obtained in the transformation 1 + 2a → 3 by thin layer chromatography (Silufol® tlc-plates, eluent: n-hexane:acetone = 2:1 [v:v]) showed that in all reactions traces of N-demethylated spiro[cyclohexadiene-dihydroacridines] were formed as by-products; they could easily be removed by recrystallization from ethanol/toluene.
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For other dealkylations of acridinium salts of the type 2 by melting or during reactions see: A. Bernthsen, Liebigs Ann. Chem., 224, 20 (1884); T. V. Stupnikova, B. P. Zemskii, Yu. B. Vysotskii, R. S. Sagitullin, and Kh. Ya. Lopatinskaya, Khim. Geterotsikl Soedin., 7, 959 (1980); S. Tamagaki, M. Ueno, and W. Tagaki, Bull. Soc. Chim. Japan, 65, 55 (1992); K. Papadopoulos, J. Nikokovonras, and D. Dimotikali, J. Prakt. Chem./Chem.-Ztg, 336, 506 (1994).
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For other dealkylations of acridinium salts of the type 2 by melting or during reactions see: A. Bernthsen, Liebigs Ann. Chem., 224, 20 (1884); T. V. Stupnikova, B. P. Zemskii, Yu. B. Vysotskii, R. S. Sagitullin, and Kh. Ya. Lopatinskaya, Khim. Geterotsikl Soedin., 7, 959 (1980); S. Tamagaki, M. Ueno, and W. Tagaki, Bull. Soc. Chim. Japan, 65, 55 (1992); K. Papadopoulos, J. Nikokovonras, and D. Dimotikali, J. Prakt. Chem./Chem.-Ztg, 336, 506 (1994).
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For other dealkylations of acridinium salts of the type 2 by melting or during reactions see: A. Bernthsen, Liebigs Ann. Chem., 224, 20 (1884); T. V. Stupnikova, B. P. Zemskii, Yu. B. Vysotskii, R. S. Sagitullin, and Kh. Ya. Lopatinskaya, Khim. Geterotsikl Soedin., 7, 959 (1980); S. Tamagaki, M. Ueno, and W. Tagaki, Bull. Soc. Chim. Japan, 65, 55 (1992); K. Papadopoulos, J. Nikokovonras, and D. Dimotikali, J. Prakt. Chem./Chem.-Ztg, 336, 506 (1994).
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0001257714
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G. N. Dorofeenko, S. V. Krivun, and V. V. Mezheritskii, Zh. Obshch. Khim., 35, 632 (1965).
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(1965)
Zh. Obshch. Khim.
, vol.35
, pp. 632
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Dorofeenko, G.N.1
Krivun, S.V.2
Mezheritskii, V.V.3
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