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2005
Halogenation
O 0235
Rearrangement of Substituted 2,4,4,6-Tetraaryl-4H-thiopyrans to Triaryl— Bromine-induced isomerization of
04- 044 -3aH-benzo[3,4]cyclopenta[1,2-b]thiophene.
thiopyran derivatives (I) results in rearranged products (II), whereas a smaller excess
of bromine only causes dibromination, cf. (IV). On the contrary, no rearranged products
are observed in the analogous intensive bromination of spiro[fluorene-9,4'-thiopyran],
possibly due to the rigid conformation of the fluorene moiety. A reaction mechanism
is proposed. — (KROULIK*, J.; CEJKA, J.; SEDMERA, P.; JEGOROV, A.;
KRATOCHVIL, B.; KUTHAN, J.; Collect. Czech. Chem. Commun. 69 (2004) 8,
1631-1642; Dep. Org. Chem., Prague Inst. Chem. Technol., CZ-166 28 Prague 6,
Czech Republic; Eng.) — H. Hoennerscheid
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