Naphthalene in THF

Sodium alkylamides can also be generated in situ by reacting the amine with sodium naphthalene in THF [207, 208]. This procedure has been used for the condensation of secondary amines with different 1,3-dienes to give high yields of monoalky-lated products without formation of 1 2 telomers. In the case of primary amines, mixtures of mono- and dialkylated products are obtained together with unidentified... 

The deprotection of the polyamine-thioethers 40a,b can also be accomplished in similar good yields with Li/naphthalene in THF (214). Cleavage of the thioether functions also commenced with [PdCl2(NCMe)2] in the case of 40b (216), and it is likely that the other macrobicycles will also undergo this metal-ion mediated cleavage reaction as well (Scheme 2). Note that this reaction cleaves only one of the two thioether bonds forming a macrocyclic ligand with one thiophenolate and one vinyl-thioether moiety, as... 

Only a few publications have appeared in which for the synthesis of reactive microgels other monomers were used than 1,4-DVB or EDMA. Hiller and Funke studied the anionic polymerization of 1,4-diisopropenylbenzene (1,4-DIPB) by n-BuLi in 1,2-dimethoxyethane and by sodium naphthalene in THF [231]. 

A wide variety of differently substituted sulfonamides 89 were very easily desulfony-lated using lithium and a catalytic amount (4%) of naphthalene in THF at temperatures ranging between —78 °C to room temperature. After hydrolysis, the expected products 90 were isolated (Scheme 38) . 

High diastereoselectivity (ds >10 1) has been achieved when the substituted pyrrole 589 was reacted with lithium and a catalytic amount (8%) of naphthalene in THF at —78 °C, being methylated with methyl iodide hence trani-product 590 was obtained (Scheme 155) . 

Lithium telluride (Li2Te) was prepared from elemental tellurium and lithium in the presence of a catalytic amount of naphthalene in THF at room temperature, and then used for the preparation of teUurophenes . 

Add slowly a solution of the 1,4-diacetoxy-2-(chloromethyl)naphthalene in THF (11 mL) and DMSO (3 mL) at such a rate that the reaction temperature remains between 40-45°C. Stir the reaction mixture at 45°C for 3 h and monitor the insertion reaction by performing an iodolysis and a hydrolysis as described in Protocol 1. 

When sodium metal is dissolved in a solution of naphthalene in THF, a green solution of a radical anion is produced. What is its structure k... 

Metalhalogen exchange of 2-, 3-, and 4-chloropyridines, and 2-chloroquinoline can be effected by naphthalene-catalyzed reductive lithiation using lithium powder in the presence of catalytic quantities of naphthalene in THF at 78 C <2000T4043>. 

In the presence of a catalyst composed of sodium naphthalene in THF, the pentenylation occurs at 20° (25). 

The problem is that, because it is extremely electron rich, this species is also extremely air sensitive, and the real quantity which is being used is not known. In addition, it reacts to give neutral naphthalene which is difficult to separate from the desired product. Finally, another problem (encountered, for instance, in cluster chemistry [58]) is that it can over-reduce the substrate and lead to decomposition whereas less powerful reducing agents are not marred by this problem. Addition of pieces of Li, Na, or K to naphthalene in THF or DME under extremely dry reaction conditions gives a green solution of the naphthalene radical anion, and concentrations of 0.1-0.5 M are employed [59]. The formation of the dianion in this reaction has also been proposed, but its formation is uncertain. It is, in any case, presumably present at low levels only, if at all. 

Triphenyltin sodium is prepared from triphenyltin bromide with sodium naphthalene in either tetrahydrofuran (THF) or 1-2-dimethoxyethane (DME), and MejSnNa is prepared in ethers using MejSnCl with Na naphthalene in THF, DME and THF-tetraglyme. Trimethyltin sodium is also prepared by adding MejSnBr dropwise with a heated pipet to Na in liq NHj at — 78°C under Ar. 

Antonietti et al.183 synthesized bicyclic PS homopolymers. They prepared difunctional PS initiated by sodium naphthalene in THF at —40 °C. The cycliza-... 

Disodium tetracarbonylferrate (Collman s reagent) is prepared by the reduction of Fe(CO)5 with sodium naphthalene in THF or sodium benzophenone ketyl in dioxane. Though it can be isolated as a white precipitate, it is usually used in THF or dioxane solution without isolation because of its highly air-sensitive and pyrophoric character. It is reported that the solubility of Na2[Fe(CO)4] is 7 x 10 M in THF and that it can be stored for moderate periods in an inert atmosphere in the dark [36]. X-ray crystallography of Na2[Fe(CO)4] (Fig. 10.2) shows that the C—Fe—C bond angle opposite to the sodium cations is significantly distorted (129.7°) [37]. However, this distortion is reduced for the potassium analogue [38]. 

S) -71, as the important intermediates. The sulphonamide 71 was cleaved to the parent amine 69 with naphthalene radical anion without racemization of the asymmetric centre adjacent to the nitrogen. The deep-green solution of naphthalene anion radical had been prepared by treating a solution of naphthalene in THF with small pieces of sodium under nitrogen. 

Preparative Methods made by addition of freshly cut Lithium metal to a solution of naphthalene in THF. Preparation can be accelerated by ultrasonication. ... 

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