Synthesis and structures of two isomeric 4-diazo-2,3,4,5-tetrahydrofuran-3- ones

Helvetica Chimica Acta

Volumn 91, Issue 9, 2008, Pages 1662-1669

  Malashikhin, Sergey A ^a,b   Linden, Anthony ^b   Heimgartner, Heinz ^b   Rodina, Ludmila L ^a   Nikolaev, Valerij A ^a  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZO TRANSFERS; MONOHYDRAZONE; TETRAHYDROFURAN; X-RAY CRYSTALLOGRAPHIES;

CRYSTALLOGRAPHY; KETONES;

X RAY CRYSTALLOGRAPHY;

2,3,4,5 TETRAHYDRO 2,2 DIMETHYL 5,5 DIPHENYLFURAN 3 ONE; 2,3,4,5 TETRAHYDRO 2,2 DIMETHYL 5,5 DIPHENYLFURAN 3,4 DIONE; 2,3,4,5 TETRAHYDRO 2,2 DIMETHYL 5,5 DIPHENYLFURAN 3,4 DIONE 3 HYDRAZONE; 4 DIAZO 2,3,4,5 TETRAHYDRO 2,2 DIMETHYL 5,5 DIPHENYLFURAN 3 ONE; 4 DIAZO 2,3,4,5 TETRAHYDRO 5,5 DIMETHYL 2,2 DIPHENYLFURAN 3 ONE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYCLIZATION; INFRARED SPECTROSCOPY; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PRIORITY JOURNAL; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 55549146441     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200890182     Document Type: Article

References (42)

1. M. Regitz, G. Maas, 'Diazo Compounds. Properties and Synthesis', Academic Press, New York, 1986.
2. H. Zollinger, 'Diazo Chemistry II. Aliphatic, Inorganic and Organometallic Compounds', Wiley-VCH, Weinheim, 1998.
3. M. P. Doyle, M. A. McKervey, T. Ye, 'Modern Catalytic Methods for Organic Synthesis with Diazo Compounds', John Wiley & Sons, New York, 1998.
4. M. Böhshar, J. Fink, H. Heydt, O. Wagner, M. Regitz, in 'Methoden der Organischen Chemie (Houben-Weyl)', Vol. E14b, Eds. D. Klamann, H. Hagemann, G. Thieme, Stuttgart, 1990, p. 961; H. Heydt, in 'Science of Synthesis', Vol. 27, Ed. A. Padwa, G. Thieme, Stuttgart, 2004, p. 843.
5. D. M. Hodgson, F. Y. T. M. Pierard, P. A. Stupple, Chem. Soc. Rev. 2001, 30, 50.
6. A. E. Koumbis, J. K. Gallos, Curr. Org. Chem. 2003, 7, 771.
7. G. Maas, Chem. Soc. Rev. 2004, 33, 183.
8. G. S. Singh, Curr. Org. Synth. 2005, 2, 377.
9. R. Huisgen, in '1,3-Dipolar Cycloaddition Chemistry', Ed. A. Padwa, Wiley-Interscience, New York, 1983, p. 1.
10. M. Regitz, H. Heydt, in '1,3-Dipolar Cycloaddition Chemistry', Ed. A. Padwa, Wiley-Interscience, New York, 1983, p. 393.
11. G. Maas, in 'Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products' (Vol. 59 of 'Chemistry of Heterocyclic Compounds'), Eds. A. Padwa, W. H. Pearson, John Wiley & Sons, New York, 2002, pp. 539-621.
12. A. G. H. Wee, Curr. Org. Synth. 2006, 3, 499.
13. J. Marco-Contelles, M. T. Molina, Curr. Org. Chem. 2003, 7, 1433.
14. X. Lei, J. A. Porco Jr., J. Am. Chem. Soc. 2006, 128, 14790.
15. T. Kumamoto, Y. Kitani, H. Tsuchiya, K. Yamaguchi, H. Seki, T. Ishikawa, Tetrahedron 2007, 63, 5189.
16. K. C. Nicolaou, H. Li, A. L. Nold, D. Pappo, A. Lenzen, J. Am. Chem. Soc. 2007, 129, 10356.
17. L. L. Rodina, I. K. Korobitsyna, Russ. Chem. Rev. (Engl. Transl.) 1967, 36, 260.
18. H. Meier, K.-P. Zeller, Angew. Chem., Int. Ed. 1975, 14, 32.
19. W. Kirmse, Eur. J. Org. Chem. 2002, 2193.
20. V. A. Nikolaev, V. V. Shevchenko, M. S. Platz, N. N. Khimich, Russ. J. Org. Chem. 2006, 42, 815.
21. M. Boukraa, W. Dayoub, A. Doutheau, Lett. Org. Chem. 2006, 3, 204.
22. S. G. Sudrik, J. Sharma, V. B. Chavan, N. K. Chaki, H. R. Sonawane, K. P. Vijayamohanan, Org. Lett. 2006, 8, 1089.
23. B. S. P. Kantharaju, V. V. S. Babu, Ind. J. Chem., Sect. B 2005, 44, 2611.
24. I. K. Korobitsina, L. L. Rodina, Zh. Org. Khim. 1965, 1, 932;
25. I. K. Korobitsina, L. L. Rodina, V. G. Shuvalova, Zh. Org. Khim. 1968, 4, 2016.
26. L. L. Rodina, V. L. Mishchenko, S. A. Malashikhin, M. Platz, V. A. Nikolaev, Russ. J. Org. Chem. 2003, 39, 1530.
27. Y. S. Zal'kind, E. D. Venus-Danilova, V. I. Ryabtseva, Zh. Obshch. Khim. 1950, 20, 2222
28. (Chem. Abstr. 1951, 45, 41391).
29. W. Jasiobedzki, Z. Matacz, Rocz. Chem. 1968, 42, 1599
30. (Chem. Abstr. 1969, 70, 37576).
31. C. K. Johnson, 'ORTEP II', Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
32. G. R. Desiraju, T. Steiner, 'The weak Hydrogen Bond in Structural Chemistry and Biology', Oxford University Press, 1999.
33. 'Encyclopedia of Reagents for Organic Synthesis', Ed. L. A. Paquette, Wiley, New York, 1995, Vol. 7, p. 5174.
34. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
35. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, New York, 1997, p. 307.
36. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435.
37. a) E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 6.1.1.1, p. 477;
38. b) D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 4.2.6.8, p. 219;
39. c) D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 4.2.4.3, p. 200.
40. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
41. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
42. G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen, 1997.