Diethylamides

LS coupling Russell-Saunders coupling. LSD Lysergic acid diethylamide. An hallucinogen. 

When butyllithium is used as a base it abstracts a proton in this case a proton attached to nitrogen The source of lithium diethylamide must be diethylamine... 

ANTIBACTERIALAGENTSSYNTHETIC - NITHOFURANS] (Vol2) 2-Acetoxy-9,10-dimethoxyl,3,4,6,7,llb-hexahydro-2FIben2o[a]qumoli2in-3-caiboxylic acid diethylamide [63-12-7]... 

FOODTOXICANTS,NATURALLYOCCURRING] EolU) Lysergic acid diethylamide... 

Titanium tetrakis(diethylamide) selectively adds to aldehydes in the presence of ketones and to the least hindered ketone in compounds containing more than one ketone. The protection is in situ, which thus avoids the usual protection-deprotec-tion sequence. Selective aldol and Grignard additions are readily performed employing this protection methodology. ... 

Tetrakis(diethylamino) titanium [(titanium tetrakis(diethylamide)] [4419-47-0] M 336.4, b 85-90"/0.1mm, 112"/0.1mm, d 0.93, n p 1.54. Dissolve in C6H6, filter if a solid separates, evaporate under reduced pressure and distil. Orange liquid which reacts violently with alcohols. [7 Chem Soc 3857 I 960.]... 

Enamines of an entirely different reactivity can be obtained by reacting compounds having co-hydroperfluoroalkyI chains with lithium diethylamide These... 

Therapeutic Function Central and respiratory stimulant Chemical Name N,N-Diethyl-4-hydroxy-3-methoxybenzamide Common Name Vanillic acid diethylamide Structural Formula coxtc HjIj... 

To a solution of 4 g of sodium in 200 ml of n-propanol is added 39 g of homovanillic acid-n-propyl ester (boiling point 160°C to 162°C/4 mm Hg) and the mixture is concentrated by evaporation under vacuum. After dissolving the residue in 200 ml of dimethylformamide and the addition of 0.5 gof sodium iodide, 26.2 g of chloracetic acid-N,N-diethylamide are added drop-wise with stirring at an internal temperature of 130°C, and the mixture is further heated at 130°C for three hours. From the cooled reaction mixture the precipitated salts are removed by filtering off with suction. After driving off the dimethylformamide under vacuum, the product is fractionated under vacuum, and 44.3 g of 3-methoxy-4-N,N-diethylcarbamido-methoxy phenyl acetic acid-n-propyl ester are obtained as a yellowish oil of boiling point 210°C to 212°C/0,7 mm Hg,... 

Table using 3-3. Enantioseparation of l-methylnaphthoyl-A. A -diethylamide and naproxene CSPs 1-11. methyl ester... 

Fig. 3-14. Separation of (A) ( )-4-(9-phenanthryl)-dihydropyrimidine 22 on chiral stationary phase CSP 11 and (B) racemic 3,5-dinitrobenzamidoalanine-A/ ,A-diethylamide on chiral stationary phase CSP 12. Conditions column 150 x 4.6 mm i.d. mobile phase dichloromethane flowrate 1 mL min...

LUMO, see Lowest unoccupied molecular orbital Lyase, 1041-1042 Lycopene, structure of, 483 Lysergic acid diethylamide, structure of, 963... 

When a solution of 25 in a 1 1 mixture of methanol and methylene chloride is exposed to periodic acid, the dithiane group is cleaved oxidatively to give, after treatment of the crude product with camphorsulfonic acid (CSA) in methanol, bisacetal 12 as a 2 1 mixture of C-12 anomers in a yield of 80% (Scheme 3). Although the conversion of 12 into 10 could be carried out on the mixture of anomers, it was found to be more convenient to carry each isomer forward separately. When 12 is treated with lithium diethylamide, the methine hydrogen adjacent to the lactone carbonyl is removed as a proton to give an enolate which is then oxidized in a completely diastereoselective fashion with Davis s oxaziridine18 to afford 11. 

The existence of a metalated epoxide was first proposed by Cope and Tiffany, to explain the rearrangement of cyclooctatetraene oxide (8) to cydoocta-l,3,5-trien-7-one (11) on treatment with lithium diethylamide. They suggested that lithiated epoxide 9 rearranged to enolate 10, which gave ketone 11 on protic workup (Scheme 5.4) [4],... 

Treatment of ris-cyclooctene oxide (15) with lithium diethylamide in ether at reflux gave endo-ris-bicyclo[3.3.0]octan-2-ol (16) in 70% yield. Under identical conditions, trons-cyclooctene oxide (17) gave exo-as-bicyclo[3.3.0]octan-2-ol (18) in 55-60% yield (Scheme 5.6) [7]. In each case, the reaction is completely stereospe-cific, with neither of the epimeric alcohols being observed, which suggests that the reactions proceed through insertion of a carbenoid (rather than the same a-li-... 

The effect of substrate structure on product profile is further illustrated by the reactions of cis- and trons-stilbene oxides 79 and 83 with lithium diethylamide (Scheme 5.17) [32]. Lithiated cis-stilbene oxide 80 rearranges to enolate 81, which gives ketone 82 after protic workup, whereas with lithiated trans-stilbene oxide 84, phenyl group migration results in enolate 85 and hence aldehyde 86 on workup. Triphenylethylene oxide 87 underwent efficient isomerization to ketone 90 [32]. 

The present procedure is a convenient, one-step method of preparing optically active /raw.s -pin ocarveol. Although lower in yield than the lithium diethylamide procedure, it is more readily adaptable to large-scale work. Moreover, the two methods are complimentary in the conditions required (neutral vs. basic) and in the overall transformation accomplished ... 

---