Selective Mono-O-acylation of C2V-symmetrical calix[4]arenediols with acylisocyanates

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2769-2772

  Yakovenko, Anton V ^a   Boyko, Vyacheslav I ^a   Kushnir, Oleg V ^a   Tsymbal, Ivan F ^a   Lipkowski, Janusz ^b   Shivanyuk, Alexander ^a   Kalchenko, Vitaly I ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^b INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; CARBAMIC ACID DERIVATIVE; ETHER DERIVATIVE; HYDROGEN;

ACYLATION; ARTICLE; CHEMICAL REACTION; HYDROGEN BOND; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 4344659544     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049030n     Document Type: Article

References (26)

1. For reviews, see: Gutsche C. D. Calixarenes Revisited; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998. Calixarenes 2001; Asfari, Z., Böhmer, V., Harowfield, J., Vicens, J., Eds; Kluwer Academic Publishers: Dordrecht, 2001. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
2. For reviews, see: Gutsche C. D. Calixarenes Revisited; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998. Calixarenes 2001; Asfari, Z., Böhmer, V., Harowfield, J., Vicens, J., Eds; Kluwer Academic Publishers: Dordrecht, 2001. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
3. For reviews, see: Gutsche C. D. Calixarenes Revisited; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998. Calixarenes 2001; Asfari, Z., Böhmer, V., Harowfield, J., Vicens, J., Eds; Kluwer Academic Publishers: Dordrecht, 2001. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
4. For reviews, see: Gutsche C. D. Calixarenes Revisited; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998. Calixarenes 2001; Asfari, Z., Böhmer, V., Harowfield, J., Vicens, J., Eds; Kluwer Academic Publishers: Dordrecht, 2001. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
5. Saadioui, M.; Shivanyuk, A.; Bohmer, V. J. Org. Chem. 1999, 64, 3774.
6. Shivanyuk, A.; Saadioui, M.; Thondorf, I.; Broda, F.; Rissanen, K.; Vysotsky, M. O.; Kolehmainen, E.; Böhmer, V. Chem. Eur. J. 2004, 10, 2138.
7. Prins, L. J.; Jolliffe, K. A.; Hulst, R.; Timmerman, P.; Reinhoudt, D. N. J. Am. Chem. Soc. 2000, 122, 3617.
8. Shivanyuk, A.; Paulus, E.; Böhmer, V.; Vogt, W. J. Org. Chem. 1998, 63, 6448.
9. Shivanyuk, A.; Paulus, E. F.; Böhmer, V. Angew. Chem., Int. Ed. 1999, 38, 2906.
10. Tsuge, O. Acyl and Thioacyl Derivatives of Isocyanates, Thiocyanates and Isothiocyanates. In The Chemistry of Cyanates and Their Thio Derivaties; Patai, S., Ed.; John Willey & Sons: Chichester, New York, Brisbane, Toronto, 1997.
11. The reaction of calixarenes with alkylisocyanates has been studied; see: König, B.; Fricke, T.; Dix, I.; Jones, P. G.; Thondorf, I. Liebigs Ann./Recueil 1997, 2315.
12. 12·2 acetone: C 50.28, H 3.49, N 5.10. Found: C 50.44, H 3.40, N 5.30.
13. Margans, J. O.; de Mendoza, J.; Pons, M.; Prados, P. J. Org. Chem. 1997, 62, 4518.
14. 6: C 68.01 H 6.99, N 1.62. Found: C 68.13, H 6.80, N 1.80.
15. -3
16. (a) Sheldrick, G. M. Acta Crystallogr. A 1990, 46, 467.
17. (b). Sheldrick, G. M SHELXL-97-A program for crystal structure refinement; University of Göttingen, Germany, 1997.
18. MMX force field was used as implemented in the PC Model program PCMODEL for Windows V. 7.50.00, 2000, Serena Software.
19. (a) Verboom, W.; Durie, A.; Egberink, R. J. M.; Asfari, Z.; Reinhoudt, D. N. J. Org. Chem. 1992, 57, 1313.
20. (b) Jacobi, R. A.; Böhmer, V.; Güttner, C.; Kraft, D.; Vogt, W. New. J. Chem. 1996, 20, 493.
21. 8: C 73.87, H 6.94. Found: C 74.02, H 6.83.
22. 6: C 75.76, H 7.72 N 2.10. Found: C 73.10, H 7.46, N 2.19.
23. 4: C 79.33, H 8.40 N 2.20. Found: C 79.44, H 8.36, N 2.17.
24. Casnati, A.; Fochi, M.; Minari, P.; Pochini, A.; Reggiani, Ungaro, R. Gazz. Chem. Ital. 1996, 126, 99-106.
25. Selective transformations of the monoacycarbamates of type 4f will be published in a due course.
26. Rudkevich, D. M. Chem. Eur. J. 2000, 6, 2679-2686.