Preparation of 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene from Two Versatile 1,3,5-Tri(halosubstituted) 2,4,6-Triethylbenzene Derivatives

Karl J. Wallace; Robert Hanes; Eric Anslyn; Jeroni Morey; Kathleen V. Kilway; Jay Siegel

doi:10.1055/s-2005-869963

PSP

Preparation of 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene from Two Versatile 1,3,5-Tri(halosubstituted) 2,4,6-Triethylbenzene Derivatives

Karl J. Wallace^a, Robert Hanes^a, Eric Anslyn*^a, Jeroni Morey^b, Kathleen V. Kilway^c, Jay Siegel^d
^a Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA
Fax: +1(512)4717791; e-Mail: anslyn@ccwf.cc.utexas.edu;
^b Department of Chemistry, Universitat de les Illes Balears, Crtra, Valldemossa, Km 7.5, Palma de Mallorca, 07122, Spain
^c Department of Chemistry, University of Missouri-Kansas City, 5100 Rockhill Rd Kansas City, MO 64110, USA
^d Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland

Abstract

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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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References

1 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