1,3-dipolar cycloadditions with 1-alkoxy-substituted nitrile ylides

Heterocycles

Volumn 47, Issue 2, 1998, Pages 781-792

  Bojkova, Nina ^a,b   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b BULGARIAN ACADEMY OF SCIENCES   (Bulgaria)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0043107497     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s(n)74     Document Type: Article

References (21)

1. H.-J. Hansen and H. Heimgartner, in '1,3-Dipolar Cycloaddition Chemistry', ed. by A. Padwa, Wiley Interscience, New York, 1984, Vol. 1, p. 177.
2. P.K. Claus, in 'Methoden der organischen Chemie (Houben-Weyl)', Band E14b, ed. by D. Klamann and H. Hagemann, G. Thieme Verlag, Stuttgart, 1990, p. 3;
3. A. Padwa, in 'Comprehensive Organic Synthesis', ed by B.M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, Vol. 4, p. 1081.
4. K.N. Houk, Topics Curr. Chem., 1979, 79, 16;
5. P. Caramella, R.W. Gandour, J.A. Hall, C.G. Deville, and K.N. Houk, J. Am. Chem. Soc., 1977, 99, 385;
6. P. Caramella and K.N. Houk, ibid., 1976, 98, 6397.
7. R. Sustmann, Pure Appl. Chem., 1974, 40, 569.
8. A. Padwa, J.R. Gasdaska, G. Haufmanns, and H. Rebello, J. Org. Chem., 1987, 52, 1027.
9. 9 The orientation of the OH and SH group does slightly influence the values; the listed values belong to the transoid conformation of the HOCN fragment.
10. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
11. J.J.P. Stewart, MOPAC V4.0, QCPE 455.
12. P. Wipf, R. Prewo, J.H. Bieri, G. Germain, and H. Heimgartner, Helv. Chim. Acta, 1988, 71, 1177.
13. N. Bozhkova and H. Heimgartner, Helv. Chim. Acta, 1989, 72, 825.
14. 10
15. 3-C(4)-atom should absorb at ca. 80-85 ppm (cf. 9a).
16. 15
17. B. Jackson, M. Märky, H.-J. Hansen, and H. Schmid, Helv. Chim. Acta, 1972, 55, 919.
18. Similar results were obtained with 2-isopropoxy-1-aza-3-oxaspiro[4.5]dec-1-en-3-one (2b) and 11. In this case, the two 1:1-adducts (ratio 1:8) must be regioisomers because no diastereoisomers can be formed using achiral starting materials.
19. D. Obrecht, R. Prewo, J.H. Bieri, and H. Heimgartner, Helv. Chim. Acta, 1982, 65, 1825.
20. T. Büchel, R. Prewo, J.H. Bieri, and H. Heimgartner, Helv. Chim. Acta, 1984, 67, 534.
21. Thermolysis of 11 in a sealed tube (4 h, 150°C) gave 14 in ca. 11% yield.