Structurally-unusual calix[4]arene derivatives generated by intra-and intermolecular McMurry reactions

Tetrahedron Letters

Volumn 37, Issue 5, 1996, Pages 645-648

  Lhoták, Pavel ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARENE;

CALIXARENE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 0030071415     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02222-8     Document Type: Article

References (14)

1. Gutsche, C. D. Calixarenes, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1989; Vol 1.
2. Vicens, J.; Böhmer, V. Eds Calixarenes: a versatile class of macrocyclic compounds; Kluwer Academic Press: Dodrecht, 1991.
3. McMurry, J. E.; Lectka, T.; Rico, J. G. J. Org. Chem., 1989, 54, 3748-3749.
4. McMurry, J. E. Chem. Rev., 1989, 89, 1513-1524.
5. Fürstner, A., Hupperts, A.; Ptock, A., Janssen, E. J. Org. Chem., 1994, 59, 5215-5229.
6. Fürstner, A.; Hupperts, A. J. Am. Chem Soc., 1995, 117, 4468-4475.
7. 3 at room temperature (96% yield), additional alkylation with propyl iodide/NaH in DMF at -5 °C (95%), lithiation with BuLi in THF and reaction with DMF (52%).
8. 4: C, 81.77; H, 7.86%. Found C, 81.46; H, 7.80%.
9. Arduini, A.; Fanni, S.; Pochini, A.; Sicuri, A. R.; Ungaro, R. Tetrahedron, 1995, 51, 7951-7958.
10. 6: C, 77.49; H, 7.76%. Found C, 77.76; H, 7.75%.
11. 3CN=10:2 v/v, 24 °C.
12. 8: C, 81.40; H, 8.01%. Found C, 81.08; H, 8.00%.
13. 4. Derivative Sa has been obtained analogously from 25,26,27,28-tetramethoxycalix[4]arene in 65% yield.
14. +).