The use of lithium and a catalytic amount of an arene is a well-established methodology for the preparation of organolithium reagents that manifest greater reactivity than the classical lithium-arene solutions. In order to rationalize this conduct, the participation of a highly reduced species, the
On the mechanism of the naphthalene-catalysed lithiation: the role of the naphthalene dianion
β Scribed by Miguel Yus; Raquel P Herrera; Albert Guijarro
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 245 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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## Abstract Metal reduction of the polycycle **2** yields a surprisingly stable dianion with intact molecular framework. This conclusion can be drawn from reoxidation experiments and from an analysis of the ^1^HβNMR. spectrum. The excess charge turns out to be distributed over both the Οβ and Οβfra
The title reaction is suggested to proceed by a reversible valence isomerization via a laterally bridge benzvalene (2). No analogous behaviour is expected for pyrene. ## cc-13C-naphthalene (1') is known to rearrange thermally into 8-13C-naphthalene (1") following a rate law in accordance with an
IlY W. 1'. JOIIISSES A S U J. IIU'ITI~X. 111 the COIIMO af it I l i ~g C iiuiiibcr of tletcriiiiiintions of iirrlilitlinlcnc 1iy the ClOliiinii-Sinit11 inet~hotl,~ tlic results olitriinctl iverc nlwnys too Iow.2 In tlicsc exlicrinicnts con1 gns freed froin nnplitliulcne or nir wns ~inssctl togrtlie
The lithiation of different phenone imines 1 with an excess of lithium powder and a catalytic amount (8 mol %) of naphthalene in the presence of several carbonyl compounds 2 in tetrahydmftuan at temperahnes ranging between -78 and 2OT leads, after hydrolysis with water, to the cotresponding l&uainoa