Safer Conditions for the Curtius Rearrangement of 1,3,5‐Benzenetricarboxylic Acid

References

• Curtius , Th. 1915 . Hydrazide und azide organischer säuren, XXX: Abhandlung: Bildung von Hydrazihydraziden und Hydraziaden dreibasischer Säuren . J. Prakt. Chem. , 91 : 39 – 102 .
   Google Scholar
• Davis , M. C. 2007 . Tricarbamate of 1,3,5‐triaminobenzene via Curtius rearrangement of trimesic acid and subsequent nitration . Synth. Commun. , 37 : 1457 – 1462 .
   Google Scholar
• Gill , J. E. , MacGillivray , R. and Munro , J. 1949 . The preparation of symmetrical aromatic triamines and triisocyanates . J. Chem. Soc. , : 1753 – 1754 .
   Web of Science ®Google Scholar
• Munro , J. and Gill , J. E. Monocyclic aromatic triisocyanates . British Patent 631,007 . October 1949 . 25
   Google Scholar
• Ambade , A. V. and Kumar , A. 2001 . An efficient route for the synthesis of hyperbranched polymers and dendritic building blocks based on urea linkages . J. Polym. Sci., Part A: Polym. Chem. , 39 : 1295 – 1304 .
   Web of Science ®Google Scholar
• van Gorp , J. J. , Vekemans , J. A. J. M. and Meijer , E. W. 2002 . C 3‐Symmetrical supermolecular architectures: Fibers and organic gels from discotic trisamides and trisureas . J. Am. Chem. Soc. , 124 : 14759 – 14769 .
   PubMed Web of Science ®Google Scholar
• van Bommel , K. J. C. , van Esch , J. H. , de Loos , M. , Heeres , A. and Feringa , B. L. Gelling agents . U.S. Patent Application Publication US 20050250857 . November 10, 2005 .
   Google Scholar
• Hassner , A. , Stern , M. , Gottlieb , H. E. and Frolow , F. 1990 . Utility of a polymeric azide reagent in the formation of di‐ and triazidomethane: Their NMR spectra and X‐ray structure of derived triazoles . J. Org. Chem. , 55 : 2304 – 2306 .
   Web of Science ®Google Scholar
• Zhang , C. Y. and Tour , J. M. 1991 . Synthesis of highly functionalized pyrazines by ortho‐lithiation reactions: Pyrazine ladder polymers . J. Am. Chem. Soc. , 121 : 8783 – 8790 .
   Google Scholar
• Yamaoka , T. , Hosoya , H. and Nagakura , S. 1968 . Spectroscopic studies on the protonation of s‐triaminobenzene . Tetrahedron , 24 : 6203 – 6213 .
   Google Scholar
• Shakhnes , A. Kh. , Vorob'ev , S. S. and Shevelev , S. A. 2006 . Selective reduction of one, two, or three nitro groups in 1,3,5‐trinitrobenzene with hydrazine hydrate . Russ. Chem. Bull., Int. Ed. , 55 : 938 – 939 .
   Web of Science ®Google Scholar
• Zengel , H.‐G. and Bergfeld , M. Process for the preparation of phloroglucinol . U.S. Patent 4,057,588 . November 8, 1977 .
   Google Scholar
• Munro , J. and Gill , J. E. Verfahren zur herstullung von monocyclischen aromatische tricarbimiden . German Patent 815,486 . October 29, 1948 .
   Google Scholar
• Shiori , T. , Ninomiya , K. and Yamada , S. 1972 . Diphenylphosphoryl azide: A new convenient reagent for a modified Curtius reaction and for the peptide synthesis . J. Am. Chem. Soc. , : 6203 – 6205 .
   PubMedGoogle Scholar
• Eaton , P. E. , Ravi Shankar , B. K. , Price , G. D. , Pluth , J. J. , Gilbert , E. E. , Alster , J. and Sandus , O. 1984 . Synthesis of 1,4‐dinitrocubane . J. Org. Chem. , 49 : 185 – 186 .
   Web of Science ®Google Scholar
• Yue , T. Y. , McLeod , D. D. , Albertson , K. B. , Beck , S. R. , Deerberg , J. , Fortunak , J. M. , Nugent , W. A. , Radesca , L. A. , Tang , L. and Xiang , C. D. 2006 . Stereoselective process for a CCR3 antagonist . Org. Process Res. Dev. , 10 : 262 – 271 .
   Web of Science ®Google Scholar
• Taylor , R. T. and Puapaiboon , U. 1998 . Polyurethane dendrimers via Curtius reaction . Tetrahedron Lett. , 39 : 8005 – 8008 .
   Web of Science ®Google Scholar
• Puapaiboon , U. and Taylor , R. T. 1999 . Characterization and monitoring reaction of polyurethane dendritic wedges and dendrimers using matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry . Rapid Commun. Mass Spectrom. , 13 : 508 – 515 .
   Google Scholar
• Clarke , H. T. and Hartmann , W. W. 1941 . 1,3,5‐Trinitrobenzene . Org. Synth. Coll. Vol. I , : 541 – 542 .
   Google Scholar
• Clarke , H. T. and Hartmann , W. W. 1941 . 2,4,6‐Trinitrobenzoic acid . Org. Synth. Coll. Vol. I , : 543 – 544 .
   Google Scholar
• Wolff , O. and Waldvogel , S. R. 2004 . Reliable protocol for the large scale synthesis of diphenylphosphoryl azide (DPPA) . Synthesis , : 1303 – 1305 .
   Google Scholar