759-22-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 603, 1984 DOI: 10.1016/S0040-4039(00)99949-0

InChI:InChI=1/C8H17NO/c1-6(2)9(7(3)4)8(5)10/h6-7H,1-5H3

Upstream product

• 830-03-5 4-nitrophenol acetate 
• 108-18-9 diisopropylamine 
• 4232-27-3 2,4-dinitrophenyl acetate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 95777-15-4 N,N-Diisopropyl-2-((R)-toluene-4-sulfinyl)-acetamide 
• 23264-07-5 N,N-Diisopropylthioacetamid 
• 34251-46-2 N,N-diisopropylphenylacetamide 

Relevant academic research and scientific papers

Reactions of aryl phenylacetates with secondary amines in MeCN. Structure-reactivity relationship in the ketene-forming eliminations and concurrent E2 and E1cb mechanisms

Elimination reactions of aryl esters of arylacetic acids 1 and 2 promoted by R2NH in MeCN have been investigated kinetically. The reactions are second-order and exhibit β = 0.44-0.84, β(lg) = 0.41-0.50, and ρ(H) = 2.0-3.6. Bronsted β and β(lg) decrease with the electron-withdrawing ability of the β-aryl substituent. Hammett ρ(H) values remain nearly the same, but the β(lg) value increases as the base strength becomes weaker. Both ρ(H) and β decrease with the change of the leaving group from 4-nitrophenoxide to 2,4-dinitrophenoxide. The results are consistent with an E2 mechanism and a reaction coordinate with a large horizontal component corresponding to proton transfer. When the base-solvent system is changed from R2NH-MeCN to R2NH/R2NH2+-70 mol% MeCN(aq), the Bronsted β, ρ(H), and β(lg) decrease. Finally, the ketene-forming elimination reactions from p-nitrophenyl p-nitrophenylacetate promoted by R2NH/R2NH2+ buffers in 70 mol% MeCN(aq) have been shown to proceed by concurrent E2 and E1cb mechanisms.

Chemistry of diamino-ligated methylpalladium(II) alkoxides and aryloxides (Part II): Methoxide formation and carbonylation reactions

Reaction of N-ligated methylpalladium(II) alkoxide and aryloxide complexes [Pd(Me)(OR)(N ～ N)] (R = Ph, CH(CF3)2; N ～ N = tmeda (N,N,N′,N′-tetramethylethylenediamine) or bpy (2,2′-bipyridyl)) with carbon monoxide produces the corresponding methylesters in high yields. The insertion takes place either into the Pd-Me bond (aryloxide complexes) or into the Pd-OR bond (alkoxide complexes). Methylpalladium(II) methoxide complexes [Pd(Me)(OMe)(N ～ N)] (N ～ N = tmeda, bpy) have been generated in situ by aryloxide- or alkoxide-methanol exchange reactions for which the equilibrium constants have been determined. The bpy-ligated methylpalladium methoxide complex undergoes insertion of CO producing either a methylpalladium methoxycarbonyl complex [Pd(Me)(CO2Me)(bpy)] (at -60°C) or an acylpalladium methoxycarbonyl complex [Pd(COMe)(CO2Me)(bpy)] (at -25°C); both carbonylated species could be isolated and characterized at low temperature.