Large cyclic oligomers of furan and acetone. X-ray crystal structure of the hexamer and first synthesis of the nonamer

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4593-4596

  Kohnke, F H ^a   La Torre, G L ^a   Parisi, M F ^a   Menzer, S ^b   Williams, D J ^b  

^a UNIVERSITY OF MESSINA   (Italy)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; FURAN; FURAN DERIVATIVE; OLIGOMER;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; OLIGOMERIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0030600149     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00885-4     Document Type: Article

References (22)

1. 1. Ackman, R. G.; Brown, W. H.; Wright, G. F. J. Org. Chem. 1955, 20, 1147-1158.
2. 2. Healy, M. D.; Rest, A. J. J. Chem. Soc., Perkin Trans. I 1985, 973-982 and references therein.
3. 3. a) Kobuke, Y.; Hanji, K.; Horiguchi, K.; Asada, M.; Nakayama, Y.; Furukawa, J. J. Am. Chem. Soc. 1976, 98, 7414-7419;
4. b) Chastrette, M.; Chastrette, F.; Sabadie, L. Organic Syntheses, Coll. Vol. 6, Noland, W. (Ed); Wiley, J.; New York 1988, 856-859 and references therein.
5. 4. a) Vogel, E.; Röhrig, P.; Sicken, M.; Knipp, B.; Herrmann, A.; Pohl, M.; Schmicker, H.; Lex, J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1651-1655;
6. b) Tanaka, S.; Tomokuni, H. J. Heterocyclic Chem. 1991, 25, 991-994;
7. c) Musau, R. M.; Whiting, A. J. Chem. Soc., Perkin Trans. I 1994, 2881-2888.
8. 5. For a review on cyclophanes containing heterocyclic units see: Newcome, G. R.; Sauer, J. D.; Roper, J. M; Hager, D. C. Chem. Rev. 1977, 77, 513-597.
9. 6. Kohnke, F. H.; Parisi, M. F.; Raymo, F. M.; Oneil, P. A.; Williams, D. J. Tetrahedron 1994; 50, 9113-9124 and references therein.
10. 4 in refluxing ether. See: Silva, R. A. Chem. Eng. News 1992, 70, 2-2.
11. 8. The oligomerization of furan with acetone is an irreversible reaction, and pure samples of L3, L6, C4, and C6, (as well as L9 and C9, v. infra) did not show any significan retro-oligomerization under the reaction conditions. Thus, the product distribution should be kinetically controlled. However, a mathematical analysis of the system is made impossible by the fact that a solid material is soon formed from the reaction mixtures. See: a) Mandolini, L. Adv. Phys. Org. Chem. 1986, 22, 1-111;
12. b) Ercolani, G.; Mencarelli, P. J. Chem Soc., Perkin Trans. II 1989, 187-191;
13. c) Ercolani, G.; Mandolini, L.; Mencarelli, P. J. Chem Soc., Perkin Trans. II 1990, 747-752.
14. 9. L3 can be distilled, L6 is purified by column chromatography, see refs. 1 and 3a respectively.
15. 10. In this case the details and the yield for the preparation of L6 were not reported; see ref. 3a.
16. 2 (toluene:hexane, 1:4) gave, in order of elution, C6 and L9. Physical and spectroscopic characteristics of C6 were identical to those reported previously: ref. 3a.
17. +·.
18. 2 = 0.086. Computations were carried out using the SHELXTL program system, version 5.03. Further details of the crystal structure investigation can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ (UK) on quoting the full journal citation.
19. 14. Hazell, A. Acta Cryst, 1989, C45, 137-140.
20. 15. This observation is consistent with the known conformational preference of furan derivatives with substituents at the 2-position. For a brief review on this topic see: Dean, F. M.; Sargent, M. V. in Comprehensive Heterocyclic Chemistry, Vol. 4, pp. 542-546; Bird, C. W.; Cheeseman, G. W. H. (Ed.), Pergamon Press, Oxford 1984.
21. +·.
22. 2; toluene:hexane, 1:3).