Selective functionalization of resorcinarene cavitands; single crystal X-ray structure of a distally functionalized cavitand

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5167-5170

  Boerrigter, Harold ^a   Verboom, Willem ^b   Van Hummel, Gerrit J ^b   Harkema, Sybolt ^b   Reinhoudt, David N ^b  

^a TNO   (Netherlands)

^b UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

RESORCINOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0030586193     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01027-1     Document Type: Article

References (15)

1. 1 For reviews see: (a) Cram, D.J.; Cram, J.M. Container Molecules and their Guests, Monographs in Supramolecular Chemistry, Vol. 4, Stoddart, J.F. (ed.), Royal Society of Chemistry: Cambridge, 1994;
2. (b) Timmerman, P.; Verboom, W.; Reinhoudt, D.N. Tetrahedron 1996, 52, 2663.
3. 2. For a recent review see: Böhmer, V. Angew. Chem. Int. Ed. Engl. 1995, 34, 713.
4. 3. Cavitands have been used in combination with calixarenes for complexation of steroids: Timmerman, P.; Brinks, E.A.; Verboom, W.; Reinhoudt, D.N. J. Chem. Soc., Chem. Commun. 1995, 417.
5. 4. (a) Timmerman, P.; Van Mook, M.G.A.; Verboom, W.; Van Hummel, G.J.; Harkema, S.; Reinhoudt, D.N. Tetrahedron Lett. 1992, 33, 3377;
6. (b) Sorrell, T.N.; Richards, J.L. Synlett 1992, 155;
7. (c) Robbins, T.A.; Cram, D.J. J. Chem. Soc., Chem. Commun. 1995, 1515.
8. 3).
9. 6. Sorrell, T.N.; Pigge, F.C. J. Org. Chem. 1993, 58, 784.
10. 7. (a) Cram, D.J.; Karbach, S.; Kim, H.-E.; Knobler, C.B.; Maverick, E.F.; Ericson, J.L.; Helgeson, R.C. J. Am. Chem. Soc. 1988, 110, 2229.
11. (b) Tunstad, L.M.; Tucker, J.A.; Dalcanale, E.; Weiser, J.; Bryant, J.A.; Sherman, J.C.; Helgeson, R.C.; Knobler, C.B.; Cram, D.J. J. Org. Chem. 1989, 54, 1305.
12. 1H NMR spectrum of the reaction mixture showed multiple signals for the protons in the methyleneoxy bridges, indicating the presence of partially brominated products. Prolonging the reaction time or using up to eight equiv of NBS did not improve the outcome of the reaction. Isolation of the tetrabrominated product from the product mixture with column chromatography remained unsuccessful.
13. 9. The partially functionalized products 5-8 show a decreased stability when stored on silica, in solution and/or contacted with air for a prolonged time, probably due to the loss of bromine. When stored shielded from light at -18°C no decomposition occurred.
14. w= 19.9%. Thermal parameters were refined anisotropically, with the exception of those belonging to solvent atoms and a number of atoms in the disordered part of the pentane chains. H-atoms were not used in the calculations. Tables with atomic coordinates, bond lengths and angles have been deposited at the Cambridge Crystallographic Data Centre.
15. 11. Burla, M.C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Polidori, G.; Spagna, R.; Viterbo, D. J. Appl. Cryst. 1989, 22, 389.