2,2,6,6-Tetramethylcyclohexanethione S-methylide, a highly hindered thiocarbonyl ylide: Two-step cycloadditions

Tetrahedron

Volumn 61, Issue 25, 2005, Pages 6143-6153

  Huisgen, Rolf ^a   Giera, Henry ^a,b   Polborn, Kurt ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b MUNICH UNIVERSITY OF APPLIED SCIENCES   (Germany)

Author keywords

1,3 Dipolar cycloadditions; Cyclic ketene imines; Dynamic 19F NMR; Thiocarbonyl ylides

Indexed keywords

ALKANE DERIVATIVE; AMPHOLYTE; CARBON; CARBONYL DERIVATIVE; CYCLOHEXANE DERIVATIVE; FLUORINE DERIVATIVE; FUMARIC ACID DERIVATIVE; KETENE DERIVATIVE; KETONE DERIVATIVE; MALEIC ACID DERIVATIVE; NITRILE; NITROGEN; THIADIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CYCLOADDITION; DIPOLE; ENERGY; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; ROTATION; SUBSTITUTION REACTION; TEMPERATURE DEPENDENCE; X RAY ANALYSIS;

EID: 20444419072     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.062     Document Type: Article

References (47)

1. 1,3-Dipolar Cycloadditions, Part 131. For part 130, see Ref. 2.
2. R. Huisgen, G. Mloston, H. Giera, E. Langhals, K. Polborn, and R. Sustmann Eur. J. Org. Chem. 2005 1519
3. Review: J. Sauer, and R. Sustmann Angew. Chem., Int. Ed. Engl. 19 1980 779
4. Brief survey: R. Huisgen V.E. Kartsev Chemistry and Biological Applications of Oxygen- and Sulfur Containing Heterocycles 2003 IBS Moscow 83 101
5. Review: R. Huisgen A. Padwa 1,3-Dipolar Cycloaddition Chemistry Vol. 1 1984 Wiley New York 1 176
6. R. Huisgen, G. Mloston, and E. Langhals J. Org. Chem. 51 1986 4085
7. R. Huisgen, G. Mloston, and E. Langhals Helv. Chim. Acta 84 2000 1805
8. R. Huisgen, J. Penelle, G. Mloston, A. Buyle-Padias, and H.K. Hall J. Am. Chem. Soc. 114 1992 266
9. G. Mloston, E. Langhals, and R. Huisgen Tetrahedron Lett. 30 1989 5373
10. R. Huisgen, G. Mloston, H. Giera, and E. Langhals Tetrahedron 58 2002 507
11. L.R. Domingo, and M.T. Picher Tetrahedron 60 2004 5053
12. R. Huisgen, E. Langhals, G. Mloston, and T. Oshima Heterocycles 29 1989 2069
13. R. Huisgen, G. Mloston, E. Langhals, and T. Oshima Helv. Chim. Acta 85 2002 2668
14. R. Huisgen, E. Langhals, and H. Nöth J. Org. Chem. 55 1990 1412
15. R. Huisgen, E. Langhals, K. Polborn, and K. Kharagiosoff Helv. Chim. Acta 87 2004 1426
16. H. Giera, R. Huisgen, E. Langhals, and K. Polborn Helv. Chim. Acta 85 2002 1523
17. R. Sustmann, W. Sicking, and R. Huisgen Eur. J. Org. Chem. 2005 in press
18. E.S. Swinbourne Analysis of Kinetic Data 1971 Th. Nelson & Sons Ltd London
19. M.M. Campbell, G.H. Anthony, and C.J.S. Brooks Org. Mass. Spectrom. 5 1971 297
20. D. Paquer, L. Morin, M. Vazeux, and C.G. Andrieu Rec. Trav. Chim. Pays-Bas 100 1981 36
21. G. Mloston, R. Huisgen, and K. Polborn Tetrahedron 55 1999 11475
22. Review: E.L. Eliel, S.H. Wilen, and L.N. Mander Stereochemistry of Organic Compounds 1994 Wiley New York pp 686-690
23. R.R. Naqvi, and P.J. Wheatley J. Chem. Soc. A 1970 2053
24. J. Lambrecht, B. Gambke, J. v. Seyerl, G. Huttner, G. Kollmannsberger-von-Nell, S. Herzberger, and J.C. Jochims Chem. Ber. 114 1981 3751
25. J.C. Jochims, J. Lambrecht, U. Burkert, L. Zsolnai, and G. Huttner Tetrahedron 40 1984 893
26. W. Runge Org. Magn. Reson. 14 1980 25
27. R. Kreuzholz, W. Schmidt-Vogt, M. Maierhofer, K. Polborn, D.S. Stephenson, and G. Szeimies Eur. J. Org. Chem. 1998 29
28. H.S. Gutowsky, and C.H. Holm J. Chem. Phys. 25 1956 1228
29. F.S.L. Anet, and V.J. Basus J. Magn. Reson. 32 1978 339
30. J.C. Jochims, and F.A.L. Anet J. Am. Chem. Soc. 92 1970 5524
31. J.C. Jochims, S. Herzberger, B. Gambke, and F.A.L. Anet Tetrahedron Lett. 1977 2255
32. P.W. Wheatley Acta Crystallogr. 7 1954 68
33. J. Firl, K. Schink, and W. Kosbahn Tetrahedron Lett. 1981 527
34. G. Wittig, and J. Meske-Schüler Liebigs Ann. Chem. 711 1968 76
35. G. Wittig, and P. Fritze Liebigs Ann. Chem. 711 1968 82
36. M. Balci, and W.M. Jones J. Am. Chem. Soc. 102 1980 7608
37. H.G. Bettinger, P.v.R. Schleyer, P.R. Schreiner, and H.F. Schaefer III J. Org. Chem. 62 1997 9267
38. H.F. Bettinger, P.R. Schreiner, P.v.R. Schleyer, and H.F. Schaefer III J. Phys. Chem. 100 1996 16147
39. B. Engels, J.C. Schöneboom, A.F. Münster, S. Groetsch, and M. Christl J. Am. Chem. Soc. 124 2002 287
40. D.M. Lemal, and L.H. Dunlap J. Am. Chem. Soc. 94 1972 6562
41. S. Proskow, H.E. Simmons, and T.L. Cairns J. Am. Chem. Soc. 88 1966 5254
42. K. Kudo Bull. Soc. Chim. Jpn 35 1962 1490
43. C.J. Ireland, K. Jones, J.S. Pizey, and S. Johnson Synth. Commun. 6 1976 185
44. R. Huisgen, X. Li, H. Giera, and H. Langhals Helv. Chim. Acta 84 2001 981
45. Sheldrick, G. M. Programs for Crystal Structure Solution; University of Göttingen, 1986, 1993.
46. Zsolnai, L.; Huttner, G. Program ZORTEP; University of Heidelberg.
47. R. Huisgen, A. Mitra, and J.R. Moran Chem. Ber. 120 1987 159