An expedient synthesis of mellitic triimides

Journal of Organic Chemistry

Volumn 73, Issue 10, 2008, Pages 3950-3953

  Rose, Kathryn G ^a   Jaber, Dina A ^a   Gondo, Chenaimwoyo A ^a   Hamilton, Darren G ^a  

^a MOUNT HOLYOKE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; DEHYDRATION; ESTERS; HEAT TREATMENT; SALTS; SYNTHESIS (CHEMICAL);

AMMONIUM SALTS; IMIDE RING; MELLITIC TRIIMIDES; ORGANIC ELECTRON ACCEPTORS;

AMIDES;

CARBOXYLIC ACID; IMIDE; MELLITIC ACID; MELLITIC TRIIMIDE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; MITSUNOBU REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

AMINES; BENZOATES; CIRCULAR DICHROISM; IMIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 43449132112     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800185v     Document Type: Article

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39. Reference 12a reports the preparation of mellitic trianhydride from mellitic acid by treatment with acetyl chloride. Our attempts to reproduce this chemistry led to inconclusive results: the poor solubility of the product, or products, eliminated the possibility of solution NMR, while both IR and solid-state NMR spectra were inconclusive. When susbstituted for mellitic acid in the preparations described here, mellitic triimides were formed in low and variable yield. However, the acid-amide materials potentially formed en route to trimides via anhydride ring opening in this case would also be formed in the initial dehydrations of the triammonium salts described in this work. Thus, initial preparation of mellitic trianhydride may now be regarded as an uneccessary embellishment of the current synthesis.
40. Reaction of the hexamethyl ester of mellitic acid with 3 equiv of p-toluidine in DMSO at 170°C for 16 h gave a 10% yield of triimide 1h. This material was spectroscopically indistinguishable from samples prepared by the current route and also proved a match to the material described in ref 6.
41. Solution NMR experiments have revealed that n-alkyl triimides are slowly attacked by primary amines. Furthermore, ref 11 describes the preparation of a mellitic hexaamide resulting from in situ solution ring opening of an intermediate imide.
42. For example, a preparation of triethylmellitic triimide (1e) that employed a 6:1 ratio of amine to mellitic acid reduced the isolated yield of product to 22%.
43. Reactants and solvents were used at exactly five times the amounts and volumes reported in the Example Preparative Procedure (Supporting Information). A 1 L flask was employed to ensure the intermediate ammonium salt was spread into a relatively thin crust on evaporation. Yield: 1.26g, 37%.
44. The lower average yields in these cases may reflect the lower nucleophilicity of anilines, when compared with amines, in the imide ring-closing reaction, though steric factors are also likely involved.
45. All IR spectra were recorded as Nujol mulls.
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