Diglyme

Nb-alkyls and aryls, e.g. MeNbCL and NbMe, Me2pCH2CH2pMe2) are known although relatively unstable. Cyclopenta-dienyl derivatives (h — C5Hs)2NbX3, (h -CjH5)Nb(CO)4 are relatively stable as is [Nb(CO)6] (NbClj + Na in diglyme + CO (pressure)). Tantalum compounds are very similar. 

Thalliumilll) niirate, T1(N03)3,3H20. Formed Tl plus cone. HNO,. Immediately hydrolysed by water but is soluble in dilute mineral acids, alcohols and diglyme. Used in oxythallation. ... 

Diglyme shown above the arrow in the equation is the solvent in this example Diglyme is an acronym for d/ethylene g/ycol dimethyl ether and its structure is CH3OCH2CH2OCH2CH2OCH3... 

Many substances have more than one ether linkage Two such compounds often used as solvents are the diethers 1 2 dimethoxyethane and 1 4 dioxane Diglyme also a commonly used solvent is a triether... 

Most metal carbonyls are synthesized in nonaqueous media. Reactive metals, such as sodium (85), magnesium (105), zinc (106), and aluminum (107,108), are usually used as reducing agents. Solvents that stabilize low oxidation states of metals and act as electron-transfer agents are commonly employed. These include diethyl ether, tetrahydrofiiran, and 2-methoxyethyl ether (diglyme). 

E)-Spiro[12,ll]letracos-13-ene (2).3 Spiro tosylhydrazone 1 (0 275 g, 0 53 mmol) in diglyme (8 mL) under N2 was treated with MeONa (0 11 g. 2 mmol) Afterl h rellux the mixture was extracted with Et20. the extract washed (brine) and evaporated to afford 0 t6 g ol 2 (91%), mp 64 se C (pentane)... 

Bu2SnNCS>20, diglyme, H2O, 100°, 82% yield.The THP group,is also cleaved by this reagent. 

NaBH4 is soluble in water, alcohols, pyridine, dioxane, dimethoxyethane, diglyme and triglyme. All these solvents, as well as aqueous tetrahydrofuran and aqueous dimethylformamide, have been used for reductions. The reductions go very slowly in di- and triglyme so these solvents are not suitable for preparative work. In some reductions in dry pyridine and dry dimethyl sulfoxide, reaction only takes place on aqueous work-up. This... 

LiBH4 reductions are usually done in tetrahydrofuran. They are also done in ethanol at —10°, ether, pyridine and diglyme. In dry pyridine the reduction of ketones goes very slowly and sometimes c)ttly takes place on aqueous work-up. " The best solvents for LitOC(CH3)3]3AlH are diglyme and tetrahydrofuran, " Reductions of unhindered ketones take... 

A cold (0°) solution of 15 g (0.039 mole) of cholest-4-en-3-one, mp 79-80°, in 200 ml of ether-benzene (8 1) is added dropwise to 0.05 mole of lithium tri-t-butoxyaluminum hydride in ether-diglyme at —40° to —50°. The mixture is allowed to stand overnight at 0° and then hydrolyzed by treatment with ice, 5 N sodium hydroxide and Rochelle salt. Evaporation of the washed and dried ether extracts and crystallization of the residue from ethyl acetate affords 13 g (87 % yield) of nearly pure cholest-4-en-3j9-ol, mp 126-129°. One recrystallization from the same solvent gives the pure product as large needles mp 131-132°, [a]o 46° reported mp 132° [a]c, 44° (benzene). 

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