2.4- Dinitrophenyl ethyl ether

Bicyclo[3.3 l]nonan-9-one, (2,4-dinitrophenyl)hydrazone (8,9) (—) Monochloroborane diethyletherate Borane, chloro-, compound with ethyl ether (8), Borane, chloro-, compound with 1,1 -oxybis[ethane] (1 1) (9) (36594-41-9). 

The simplest example of a functional micelle is (49), previously demonstrated to be more effective than its trimethylammonium analogue in both esterolysis and bimolecular elimination reactions. It has now been demonstrated that micelles of (49) are more effective catalysts for the hydrolysis of p-nitrobenzoyl phosphate dianion at high pH than non-functional surfactants. " 2,4-Dinitrochloro- and fluoro-benzene react with micelles of (49) at high pH 10" times faster than with hydroxide ion at a comparable external pH. The initial product is (50) and this in turn is hydrolysed in micelles 2.6 x 10 times faster than is 2,4-dinitrophenyl 2-(trimethylammonium)ethyl ether in water at pH 12. Acyl transfer between p-nitrophenyl acetate and (49) gives an intermediate whose hydrolysis is not micelle catalysed. In contrast to the rate acceleration observed in that case, hydrolysis of p-nitrophenyl acetate is inhibited by micelles of (51) since the phenoxide nucleophile is weak and at the reaction pH its micelles are zwitterionic, not cationic. Synthesis of functional choline-type micelles is facilitated by the use of sulphonate (52), which is reactive towards thiophenoxide in aqueous micelles, but its water-insoluble trifluoromethanesulphonate reacts with a range of anions under phase-transfer conditions. " ... 

Most examples of the Bradsher cycloaddition reaction have utilized fused polycyclic aromatics as the cationic aza-diene fragment. Falck and co-workers have reported that one can carry out this reaction using monocyclic quaternary aza-aromatics. The application of this methodology was illustrated using the A -(2,4-dinitrophenyl) salt of A, A -diethylnicotin-amide 3 and ethyl nicotinate 4 in conjunction with enol ethers. The reaction proceeded at room temperature to generate adducts 5. This was the result of the exo-addition at the C2-C5 positions of the pyridyl ring. The resultant iminium ion was then trapped by the methanolic solvent. 

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