1H-naphtho[2,1-b]thiete and 2H-naphtho[2,3-b]thiete- synthesis and reactivity
1994; Elsevier BV; Volume: 35; Issue: 14 Linguagem: Inglês
10.1016/s0040-4039(00)76785-2
ISSN1873-3581
Autores Tópico(s)Photochromic and Fluorescence Chemistry
ResumoThe title compounds 4 and 8 are obtained by flash vacuum pyrolysis of the corresponding hydroxymethylthionaphthols 3 and 7. Whereas 4 shows a smooth ring opening on heating, 8 is thermally stable but reacts photochemically. The different behavior is explained on the basis of an MNDO calculation. The valence isomers 4′ and 8′ represent thioquinonemethides, which are highly reactive components in [12π + 2π]cycloaddition processes (4 → 9, 10, 11; 8 → 12).
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