6533b858fe1ef96bd12b6195
RESEARCH PRODUCT
1H-naphtho[2,1-b]thiete and 2H-naphtho[2,3-b]thiete- synthesis and reactivity
Herbert MeierAxel Mayersubject
Valence (chemistry)Flash vacuum pyrolysisChemistryStereochemistryOrganic ChemistryDrug DiscoverySous videMNDOReactive componentsReactivity (chemistry)BiochemistryMedicinal chemistryCycloadditiondescription
Abstract The 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).
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1994-04-01 | Tetrahedron Letters |