Reducing agents naphthalide salts

This approach frequently leads to the most active metals as the relatively short reduction times at low temperatures leads to reduced sintering of the metal particles and hence higher reactivity. Fujita, et aL(62) have recently shown that lithium naphthalide in tqluepe can be prepared by sonicating lithium, naphthalene, and N, N, N, N-tetramethylethylene-diamine (TMEDA) in toluene. This allows reductions of metal salts in hydrocarbon solvents. This proved to be especially beneficial with cadmium(49). An extension of this approach is to use the solid dilithium salt of the dianion of naphthalene. Use of this reducing agent in a hydrocarbon solvent is essential in the preparation of highly reactive uranium(54). This will be discussed in detail below. 

In solution, the reduction of fullerenes is typically performed in etheral solvents (e.g., tetrahydrofuran, dimethoxyethane) [138] or liquid ammonia [139]. Using Li as a reducing agent it is possible to reach the highest reduction step, the hexa-anion. With the other alkali metals this was observed only when naphthalide salt was added [140]. The reduction of C o and all the higher fullerenes to their hexa-anions was first made possible by sonication with excess Li [16] and later by adding a small amount of 2 as an electron shuttle (vide supra). 

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