Synthesis of medium-size macrocycles by cinnamate [2 + 2] photoaddition

Liebigs Annales

Volumn , Issue 8, 1996, Pages 1231-1233

  König, Burkhard ^a   Leue, Stefanie ^a   Horn, Clemens ^a   Caudan, Arnaud ^b   Desvergne, Jean Pierre ^b   Bouas Laurent, Henri ^b  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b CNRS   (France)

Author keywords

Cinnamates; Enediynes; Macrocycles; 2 + 2 Photoadditions

Indexed keywords

EID: 4243293119     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960802     Document Type: Article

References (19)

1. M. D. Cohen, G. M. Schmidt, F. I. Sonntag, J. Chem. Soc. 1964, 2000-2013.
2. [2a] H. Greiving, H. Hopf, P. G. Jones, P. Bubenitschek, J.-P. Desvergne, H. Bouas-Laurent, J. Chem. Soc., Chem. Commun. 1994, 1075-1076.
3. [2b] H. Greiving, H. Hopf, P. G. Jones, P. Bubenitschek, J.-P. Desvergne, H. Bouas-Laurent, Liebigs Ann. 1995, 1949-1956.
4. [2c] H. Hopf, H. Greiving, P. Bubenitschek, P. G. Jones, Angew. Chem. 1995, 107, 742-744;
5. Angew. Chem. Int. Ed. Engl. 1995, 34, 685-687.
6. Selected examples of photochemical reactions of tethered cinnamic acid derivatives: [3a] J. Rennert, S. Soloway, I. Waltcher, B. Leong, J. Am. Chem. Soc. 1972, 94, 7242-7244.
7. [3b] J. A. Ors, R. Srinivasan, J. Chem. Soc., Chem. Commun. 1978, 400-401.
8. [3c] M. Kuzuya, N. Yokota, M. Tanaka, T. Okuda, Chem. Lett. 1985, 1467-1470.
9. [3d] S. Akabori, T. Kumagai, Y. Habata, S. Sato, J. Chem. Soc., Perkin Trans. 1, 1989, 1497-1505.
10. [3e] S. A. Fleming, S. C. Ward, Tetrahedron Lett. 1992, 33, 1013-1016.
11. 1H-NMR spectral data. The chemical shifts and the split pattern of the cyclobutane ring protons are consistent with those of dimethyl β-truxinate: [4a] D. A. Ben-Efraim, B. S. Green, Tetrahedron 1974, 30, 2357-2364. Furthermore, alkaline hydrolysis of the bisester gave a truxinic acid isomer with m.p. 208°C. Only β-truxinic acid shows a melting point in this range.
12. [4b] R. Stoermer, E. Laage, Ber. Dtsch. Chem. Ges. 1921, 54B, 77-85 (m.p. 209-210°C).
13. [4c] G. Kaupp, Angew. Chem. 1992, 104, 606-609;
14. Angew. Chem. Int. Ed. Engl. 1992, 31, (m.p. 210°C).
15. B. König, H. Hollnagel, B. Ahrens, P. G. Jones, Angew. Chem. 1995, 107, 2763-2765;
16. Angew. Chem. Int. Ed. Engl. 1995, 34, 2538-2540.
17. H. Hopf, C. Werner, P. Bubenitschek, P. G. Jones, Angew. Chem. 1995, 107, 2592-2594;
18. Angew. Chem. Int. Ed. Engl. 1995, 34, 2367-2369.
19. M. E. Maier, Synlett 1995, 13-26.