Cyclopropyl building blocks in organic synthesis. Part 81: Striving for unusually strained oxiranes: Epoxidation of spirocyclopropanated methylenecyclopropanes

Tetrahedron

Volumn 58, Issue 35, 2002, Pages 7001-7007

  Frank, Daniel ^a   Kozhushkov, Sergei I ^a   Labahn, Thomas ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Alkenes; Epoxidations; Heterotriangulanes; Peroxides; Small ring systems

Indexed keywords

1 OXADISPIRO[2.0.2.1]HEPTANE; 1 OXATRISPIRO[4.0.2.0.2.0]UNDECAN 2 ONE; 3 CHLOROBENZOIC ACID; BICYCLO COMPOUND; CYCLOPROPANE DERIVATIVE; DIMETHYLDIOXIRANE; DISPIRO[3.0.3.1]OCTAN 1 ONE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; HEPTANE; LITHIUM DERIVATIVE; LITHIUM IODIDE; PENTASPIRO[2.1.0.2.0.2.0.0.2.0]TETRADECAN 4 ONE; SPIRO COMPOUND; SPIRO[2.3]HEPTAN 4 ONE; TRISPIRO[3.0.2.0.2.0]DECAN 1 ONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLOPROPANATION; ENVIRONMENTAL TEMPERATURE; EPOXIDATION; HIGH TEMPERATURE; ORGANIC CHEMISTRY; OXIDATION; PRIORITY JOURNAL; SYNTHESIS; THERMOSTABILITY;

EID: 0037178959     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00695-6     Document Type: Article

References (48)

1. Part 80: von Seebach M., de Meijere A., Grigg R. Eur. J. Org. Chem. 2002;. in press. Part 79: de Meijere A., Williams C.M., Chaplinski V., Kourdioukov A., Sviridov S.V., Savtchenko A., Kordes M., Stratmann C. Eur. J. Chem. 8:2002;3789-3801.
2. Part 80: von Seebach M., de Meijere A., Grigg R. Eur. J. Org. Chem. 2002;. in press. Part 79: de Meijere A., Williams C.M., Chaplinski V., Kourdioukov A., Sviridov S.V., Savtchenko A., Kordes M., Stratmann C. Eur. J. Chem. 8:2002;3789-3801.
3. Greenberg A., Liebman J.F. Strained Organic Molecules, Organic Chemistry Series. Vol. 38:1978;Academic, New York.
4. (a) Cremer D., Kraka E. Liebman J.F., Greenberg A., Structure and Reactivity. 1988;65-138 VCH, Weinheim,
5. (b) Cremer D. Tetrahedron. 44:1988;7427-7454.
6. de Meijere A. Angew. Chem. 91:1979;867-884. Angew. Chem., Int. Ed. Engl. 1979, 18, 809-826.
7. Danishefsky S. Acc. Chem. Res. 12:1979;66-72.
8. Carbocyclic Three-Membered Ring Compounds. de Meijere A., Methods of Organic Chemistry (Houben-Weyl). Vols. E17a-c:1997;Georg Thieme, Stuttgart.
9. (a) von Baeyer A. Chem. Ber. 18:1885;2269-2281
10. (b) Huisgen R. Angew. Chem. 98:1986;297-311. Angew. Chem., Int. Ed. Engl. 1986, 25, 297-311
11. (c) Wiberg K.B. Angew. Chem. 98:1986;312-322. Angew. Chem., Int. Ed. Engl. 1986, 25, 312-322
12. (d) Halton B. Halton B., Advances in Strain in Organic Chemistry. Vol. 1:1991;1-17 JAI, Greenwich.
13. (a) Review: de Meijere A., Kozhushkov S.I. Chem. Rev. 100:2000;93-142
14. (b) Tamm M., Thutewohl M., Ricker C., Bes M.T., de Meijere A. Eur. J. Org. Chem. 1999;2017-2024.
15. (a) Aue D.H., Meshishnek M.J., Shellhamer D.F. Tetrahedron Lett. 1973;4799-4802. and Ref. 3 cited therein
16. (b) Crandall J.K., Conover W.W. J. Org. Chem. 43:1978;3533-3535
17. (c) Salaün J.R., Conia J.-M. J. Chem. Soc., Chem. Commun. 1971;1579-1580
18. (d) Salaün J.R., Champion J., Conia J.-M. Org. Synth. 57:1977;36-40.
19. (e) Review: Salaün J.R. Rappoport Z., The Chemistry of the Cyclopropyl Group. 1987;809-878 Wiley, New York,
20. (f) Trost B.M. Top. Curr. Chem. 133:1986;3-82.
21. (a) Nemoto H., Fukumoto K. Synlett. 1997;863-875
22. (b) Nemoto H., Miyata J., Hakamata H., Nagamochi M., Fukumoto K. Tetrahedron. 51:1995;5511-5522
23. (c) Bernard A.M., Floris K., Frongia A., Piras P.P. Synlett. 1998;668-670.
24. (a) Erden I., de Meijere A., Rousseau G., Conia J.-M. Tetrahedron Lett. 21:1980;2501-2504
25. (b) Hofland A., Steinberg H., de Boer T.J. Recl. Trav. Chim. Pays-Bas. 104:1985;350-352.
26. de Meijere A., Erden I., Weber W., Kaufmann D. J. Org. Chem. 53:1988;152-161.
27. Review: de Meijere A., Kozhushkov S.I., Khlebnikov A.F. Top. Curr. Chem. 207:2000;89-147.
28. Denis J.M., Le Perchec P., Conia J.-M. Tetrahedron. 33:1977;399-408.
29. Gajewski J.J., Oberdier J.P. J. Am. Chem. Soc. 94:1972;6053-6059.
30. de Meijere A., von Seebach M., Zöllner S., Kozhushkov S.I., Belov V.N., Boese R., Benet-Buchholz J., Yufit D.S., Howard J.A.K. Chem. Eur. J. 7:2001;4021-4034. and Ref. 16 cited therein.
31. Review: Adam W., Hadjiarapoglou L. Top. Curr. Chem. 164:1993;45-62.
32. -3. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited as supplementary publication no. CCDC-182317 (11), CCDC-182315 (23), and CCDC-182316 (26) with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
33. Denis J.M., Le Perchec P., Conia J.-M. Tetrahedron. 33:1977;399-408.
34. de Meijere A. Angew. Chem. 91:1979;867-884. Angew. Chem., Int. Ed. Engl. 1979, 18, 809-826.
35. For reviews see: (a) Klunder A.J.H., Zwanenburg B. de Meijere A., Methods of Organic Chemistry (Houben-Weyl). Vol. E17c:1997;2419-2537 Georg Thieme, Stuttgart, (b) Fitjer L. de Meijere A., Methods of Organic Chemistry (Houben-Weyl). Vol. E17e:1997;251-317 Georg Thieme, Stuttgart.
36. For reviews see: (a) Klunder A.J.H., Zwanenburg B. de Meijere A., Methods of Organic Chemistry (Houben-Weyl). Vol. E17c:1997;2419-2537 Georg Thieme, Stuttgart, (b) Fitjer L. de Meijere A., Methods of Organic Chemistry (Houben-Weyl). Vol. E17e:1997;251-317 Georg Thieme, Stuttgart.
37. (a) Zöllner S., Buchholz H., Boese R., Gleiter R., de Meijere A. Angew. Chem. 103:1991;1544-1546. Angew. Chem., Int. Ed. Engl. 1991, 30, 1518-1520
38. (b) von Seebach M., Kozhushkov S.I., Boese R., Benet-Buchholz J., Yufit D.S., Howard J.A.K., de Meijere A. Angew. Chem. 112:2000;2617-2620. Angew. Chem., Int. Ed. Engl. 2000, 39, 2495-2498.
39. Zöllner, S., Dissertation, Universität Hamburg, 1991.
40. Kozhushkov, S.; Späth, T.; Fiebig, T.; Galland, G.; Ruasse, M.-F.; Xavier, P.; Apeloig, Y.; de Meijere, A. J. Org. Chem., 2002, 67, 4100-4114.
41. 12 In this case intermediate of the type 25 was presumably formed directly from 6a and the oxidizing agent.
42. Cole K.C., Gilson D.F.R. Can. J. Chem. 54:1976;657-664.
43. Brown J.M., Conn A.D., Pilcher G., Leitao M.L.P., Meng-Yan Y. J. Chem. Soc., Chem. Commun. 1989;1817-1819.
44. Boese R., Haumann T., Kozhushkov S., Jemmis E.D., Kiran B., de Meijere A. Liebigs Ann. 1996;913-919.
45. Allen F.H. Acta Crystallogr. B. 36:1980;81-96.
46. Beckhaus H.-D., Rüchardt C., Kozhushkov S.I., Belov V.N., Verevkin S.P., de Meijere A. J. Am. Chem. Soc. 117:1995;11854-11860.
47. de Meijere A., Kozhushkov S.I., Faber D., Bagutskii V., Boese R., Haumann T., Walsh R. Eur. J. Org. Chem. 2001;3607-3614.
48. de Meijere A., Kozhushkov S.I., Spaeth T., Zefirov N.S. J. Org. Chem. 58:1993;502-505.