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Synthesis 2005(12): 2080-2083
DOI: 10.1055/s-2005-869963
DOI: 10.1055/s-2005-869963
PSP
© Georg Thieme Verlag Stuttgart · New York
Preparation of 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene from Two Versatile 1,3,5-Tri(halosubstituted) 2,4,6-Triethylbenzene Derivatives
Further Information
Received
19 November 2004
Publication Date:
13 June 2005 (online)
Publication History
Publication Date:
13 June 2005 (online)
Abstract
The use of 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene and the intermediates 1,3,5-tris(halomethyl)-2,4,6-triethylbenzene (halo = bromo and chloro) compounds, have been utilized as scaffolds for many molecular receptors. We report here for the first time a detailed practical synthetic procedure, starting from benzene, and in four straightforward steps, to prepare 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene, a very versatile molecular scaffold. The added advantage is the limited chromatography in the purification procedure.
Key words
molecular receptors - pinwheel - substituted aromatic alkyl halides - Staudinger reduction - triethylbenzene scaffold
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Hennrich G.Anslyn EV. Chem. Eur. J. 2002, 8: 2219 - 2
Stack TDP.Hou Z.Raymond KN. J. Am. Chem. Soc. 1993, 115: 6466 - 3
Walsdorff C.Saak W.Pohl S. J. Chem. Soc., Dalton Trans. 1997, 1857 - 4
Wallace KJ.Belcher WJ.Turner DR.Syed KF.Steed JW. J. Am. Chem. Soc. 2003, 125: 9699 - 5
MacNicol DD.Wilson DR. J. Chem. Soc., Chem. Commun. 1976, 355 - 6
MacNicol DD.Hardy ADU.Wilson DR. Nature 1977, 266: 611 - 7
Zhong ZL.Anslyn EV. J. Am. Chem. Soc. 2002, 124: 9014 - 8
Zhong ZL.Anslyn EV. Angew. Chem. Int. Ed. 2003, 42: 3005 - 9
Fuson RC.House HO.Melby LR. J. Am. Chem. Soc. 1953, 75: 5954 - 10
Kilway KV.Siegel JS. Tetrahedron 2001, 57: 3615 - 11
Walsdorff C.Saak W.Pohl S. J. Chem. Res., Miniprint 1996, 1601 - 12
Metzger A.Lynch VM.Anslyn EV. Angew. Chem. Int. Ed. 1997, 36: 862 - 13
van der Made AW.van der Made RH. J. Org. Chem. 1993, 58: 1262 - 14
Cabell L.Best AM.Lavigne DJ.Schneider JS.Perreault ED.Monahan MMK.Anslyn EV. J. Chem. Soc., Perkin Trans. 2 2001, 315