1H and 13C NMR spectra and one-bond 13C,13C coupling constants of (E)-2-alken-4-yn-1-ols, (E)-2-alken-4-yn-1-yl acetates and (E)-2-alken-4-yn-1-als

Magnetic Resonance in Chemistry

Volumn 35, Issue 10, 1997, Pages 712-716

  Poleschner, Helmut ^a   Heydenreich, Matthias ^b  

^a Inst Org Chem Strukturanalytik ^*  (Germany)

^b UNIVERSITY OF POTSDAM   (Germany)

Author keywords

(E) 2 alken 4 yn 1 als; (E) 2 alken 4 yn 1 ols; (E) 2 alken 4 yn 1 yl acetates; (E) 2 penten 4 yn 1 ol; 13C NMR; 1J(13C,13c) coupling constants; NMR

Indexed keywords

CHEMICAL SHIFT; HYDROCARBONS;

(E)-2-ALKEN-4-YN-1-ALS; (E)-2-ALKEN-4-YN-1-OLS; (E)-2-ALKEN-4-YN-1-YL ACETATE; (E)-2-PENTEN-4-YN-1-OL; 13C; 13C NMR; 1J(13C,13C) COUPLING CONSTANT; COUPLING CONSTANTS; NMR CHEMICAL SHIFTS; NMR SPECTRUM;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0031520701     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1097-458x(199711)35:10<712::aid-omr159>3.3.co;2-o     Document Type: Article

References (39)

1. L. Brandsma and H. D. Verkruijsse, Synthesis of Acetylenes, Allenes and Cumulenes, p. 78. Elsevier, Amsterdam (1981).
2. L. Brandsma, Preparative Acetylenic Chemistry, 2nd ed., p. 63. Elsevier, Amsterdam (1992).
3. K. C. Nicolaou, J. Y. Ramphal, N. A. Petasis and C. N. Serhan, Angew. Chem. 103, 1119 (1991).
4. E. J. Corey and G. Schmidt, Tetrahedron Lett., 399 (1979).
5. G. Fouquet and M. Schlosser, Angew. Chem. 86, 50 (1974).
6. M. van Klaveren, E. S. M. Persson, A. del Villar, D. M. Grove, J.-E. Bäckvall and G. van Koten, Tetrahedron Lett. 36, 3059 (1995).
7. H. Arn, M. Tóth and E. Prisner, List of Sex Pheromones of Lepidoptera and Related Attractants, 2nd ed. International Organization of Biological Control, Montfavet (1992).
8. E. Butenandt and E. Hecker, Angew. Chem. 73, 349 (1961).
9. Reviews on pheromone research: (a) R. Rossi, Synthesis, 817 (1977);
10. (b) C. A. Henrick, Tetrahedron 33, 1845 (1977);
11. H. J. Bestmann and O. Vostrowsky, in Chemie der Pflanzenschutz-und Schädlingsbekämpfungsmittel, edited by R. Wegler, Vol. 6. Springer, Berlin (1981);
12. H. E. Hummel and T. A. Miller (Eds), Techniques in Pheromone Research. Springer, New York (1984);
13. (e) A. B. Attygalle and E. D. Morgan, Angew. Chem. 100, 475 (1988);
14. (f) K. Mori, in The Total Synthesis of Natural Products, edited by J. ApSimon, Vol. 9. Wiley, Chichester (1992).
15. M. T. W. Hearn and J. L. Turner, J. Chem. Soc., Perkin Trans. 2, 1027 (1976).
16. H. Poleschner, M. Heydenreich and D. Martin, Synthesis, 1231 (1991).
17. R. Radeglia, H. Poleschner and M. Heydenreich, Magn. Reson. Chem. 29, 1028 (1991).
18. R. Radeglia, H. Poleschner and F. Theil, J. Prakt. Chem. 335, 673 (1993).
19. R. Radeglia, H. Poleschner and G. Haufe, Magn. Reson. Chem. 31, 639 (1993).
20. R. Radeglia, H. Poleschner and G. Haufe, Magn. Reson. Chem. 31, 1054 (1993).
21. H. Poleschner and M. Heydenreich, Magn. Reson. Chem. 33, 917 (1995).
22. H. Günther, NMR-Spektroskopie, 3rd ed., pp. 108ff. Georg Thieme, Stuttgart (1992).
23. H. Günther, NMR-Spektroskopie, 3rd ed., pp. 121ff. Georg Thieme, Stuttgart (1992).
24. J. Buddrus and H. Bauer, Angew. Chem. 99, 632 (1987).
25. 13C-NMR-Spektroskopie, pp. 493ff. Georg Thieme, Stuttgart (1984).
26. E. Breitmaier and W. Voelter, Carbon-13 NMR Spectroscopy, 3rd ed., pp. 147ff. VCH, Weinheim (1990).
27. (a) Z. Biedrzycka and K. Kamienska-Trela, Spectrochim. Acta, Part A 42, 1323 (1986);
28. (b) K. Kamienska-Trela, Z. Biedrzycka, R. Machinek, B. Knieriem and W. Lüttke, Org. Magn. Reson. 22, 317 (1984).
29. A. Sebald and B. Wrackmeyer, Spectrochim. Acta, Part A 37, 365 (1986).
30. J. Lambert and M. Klessinger, Magn. Reson. Chem. 25, 456 (1987).
31. K. Kamienska-Trela, Annu. Rep. NMR Spectrosc. 30, 131 (1995).
32. L. B. Krivdin and G. A. Kalabin, Prog. Nucl. Magn. Reson. Spectrosc. 21, 293 (1989).
33. B. Wrackmeyer and K. Horchler, Progr. Nucl. Magn. Reson. Spectrosc. 22, 209 (1990).
34. W. Höboldt, R. Radeglia and D. Klose, J. Prakt. Chem. 318, 519 (1976).
35. M. T. W. Hearn, J. Magn. Reson. 22, 521 (1976).
36. E. Breitmaier and W. Voelter, Carbon-13 NMR Spectroscopy, 3rd ed., pp. 208, 217. VCH, Weinheim (1990).
37. F. Bohlmann and M. Brehm, Org. Magn. Reson. 12, 535 (1979).
38. L. Brandsma and H. D. Verkruijsse, Synthesis of Acetylenes, Allenes and Cumulenes, p. 58. Elsevier, Amsterdam (1981).
39. H. J. Bestmann, W. Stransky and O. Vostrowsky, Chem. Ber. 109, 1694 (1976).