Monodeoxygenation of spiro adamantane-1,2-dioxetanes induced by aminium salt
β Scribed by Luigi Lopez; Gianluca M. Farinola; Angelo Nacci; Stefano Sportelli
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 384 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0040-4020
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β¦ Synopsis
The reactions of 4,
2]
-dioxetane] (la) and bi-~lamantylidene-l,2-dioxetane (2a) in dichloromethane, at different reaction temperatures, with tris-(2,4-dibromophenyl) aminium hexachioroantimonate A afford high yields of the rearranged ketones 2-methyladmnantyl-methyl ketone (3) and spiro[adamantane-2,4'-homoadamantan-5'-one] (8), respectively. A cation radical monedeoxygenation process is suggested.
π SIMILAR VOLUMES
The aminium salt induced reactions of stilbenes (la-d), affording a mixture of indane (2a--e) and/or tetrahydronaphthalene derivatives (3a,c,d), were found to occur with remarkably higher efficiency in 1,1,1,3,3,3hexafluoropropan-2-ol (HFP) than, if at all, in dichloromethane (DCM) solutions. This s
Spiro[1,2-dioxetane-3,1 0 -dihydroisobenzofuran] syn-3 bearing a hydroxy group at the 6-position (as a model syn-rotamer of parent dioxetane 4 bearing a 3-hydroxyphenyl group) and its isomer anti-3 (as a model anti-rotamer of 4) were synthesized. When these spiro-dioxetanes were treated with tetrabu