A mild and efficient synthesis of buta-1,3-dienes substituted with a terminal pentafluoro-6-sulfanyl group

Synthesis

Volumn , Issue 22, 2010, Pages 3906-3912

  Ponomarenko, Maxim V ^a,b   Serguchev, Yurii A ^a   Röschenthaler, Gerd Volker ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^b JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

alkenes; butadienes; elimination; pentafluorosulfanyl group

Indexed keywords

ALKENES; DEHYDROBROMINATION; EFFICIENT SYNTHESIS; ELIMINATION; PENTAFLUOROSULFANYL GROUP; SYNTHETIC SEQUENCE;

BUTADIENE; ORGANIC POLYMERS;

OLEFINS;

1 (PENTAFLUORO LAMBDA6 SULFANYL)ALK 1 ENE DERIVATIVE; 1 (PENTAFLUORO LAMBDA6 SULFANYL)ALKA 1,3 DIENE; 1 [2 (PENTAFLUORO LAMBDA6 SULFANYL)VINYL]CYCLOHEXANE; 1,2 DIBROMO 1 (PENTAFLUORO LAMBDA6 SULFANYL)ALKANE DERIVATIVE; 1,2 DIBROMO 3 METHYL 1 (PENTAFLUORO LAMBDA6 SULFANYL)BUTANE; 1,3 BUTADIENE DERIVATIVE; 2 CHLORO 1 (PENTAFLUORO LAMBDA6 SULFANYL)ALKANE DERIVATIVE; 2 CHLORO 3 METHYL 1 (PENTAFLUORO LAMBDA6 SULFANYL)BUTANE; 3 BROMO 1 (PENTAFLUORO LAMBDA6 SULFANYL)ALK 1 ENE DERIVATIVE; 3 METHYL 1 (PENTAFLUORO LAMBDA6 SULFANYL)BUT 1 ENE; 3 METHYL 1 (PENTAFLUORO LAMBDA6 SULFANYL)BUTA 1,3 DIENE; [1 BROMO 3 (PENTAFLUORO LAMBDA6 SULFANYL)PROP 3 ENYL]CYCLOHEXANE; [1 CHLORO 2 (PENTAFLUORO LAMBDA6 SULFANYL)ETHYL]CYCLOHEXANE; [1,2 DIBROMO 1 (PENTAFLUORO LAMBDA6 SULFANYL)ETHYL]CYCLOHEXANE; [2 (PENTAFLUORO LAMBDA6 SULFANYL)VINYL]CYCLOHEXANE; [2 BROMO 3 (PENTAFLUORO LAMBDA6 SULFANYL)PROP 3 ENYL]CYCLOHEXANE; [2 BROMO 4 (PENTAFLUORO LAMBDA6 SULFANYL)BUT 3 ENYL]BENZENE; [2 CHLORO 3 (PENTAFLUORO LAMBDA6 SULFANYL)PROPYL]CYCLOHEXANE; [3 (PENTAFLUORO LAMBDA6 SULFANYL)PROP 2 ENYL]CYCLOHEXANE; [3 (PENTAFLUORO LAMBDA6 SULFANYL)PROP 2 ENYLIDENE]CYCLOHEXANE; [3 CHLORO 4 (PENTAFLUORO LAMBDA6 SULFANYL)BUTYL]BENZENE; [4 (PENTAFLUORO LAMBDA6 SULFANYL)BUT 3 ENYL]BENZENE; [4 (PENTAFLUORO LAMBDA6 SULFANYL)BUTA 1,3 DIENYL]BENZENE; ALKENE DERIVATIVE; BROMINE; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; BROMINATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DEBROMINATION; DECHLORINATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 78149455927     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258254     Document Type: Article

References (34)

1. Müller M, Faeh C, Diederich F, Science 2007 317 1881
2. Purser S, Moore P R., Swallow S, Gouverneur V, Chem. Soc. Rev. 2008 37 320
3. Kirk K L., Org. Process Res. Dev. 2008 12 305
4. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Application Kirsch P Wiley-VCH Weinheim 2004
5. Ye C, Gard G L., Winter R W., Syvret R G., Twamley B, Shreeve J M., Org. Lett. 2007 9 3841
6. Winter R W., Dodean R A., Gard G L., In Fluorine-Containing Synthons, ACS Symposium Series 911 Soloshonok V A. American Chemical Society Washington DC 2005 87-118
7. Kirsch P, Röschenthaler G.-V, In Current Fluoroorganic Chemistry - New Synthetic Directions, Technologies, Materials, and Biological Applications, ACS Symposium Series 949 Soloshonok V A. Mikami K Yamazaki T Welch J T. Honek J F. American Chemical Society Washington DC 2007 221
8. Welch J T., Lim D S., Bioorg. Med. Chem. 2007 15 6659
9. Lal G S., Syvret R G., Chim. Oggi 2008 26 26
10. Lentz D, Seppelt K, In Chemistry of Hypervalent Compounds Akiba K Wiley-VCH Weinheim 1999 295-325
11. Salmon R, WO 9,306,089 1993, Howard M H. Jr., Stevenson T M., WO 9,516,676 1995
12. Crowley P J., Mitchell G, Salmon R, Worthington P A., Chimia 2004 58 138
13. Kirsch P, Binder J T., Lork E, Röschenthaler G.-V, [nl]J. Fluorine Chem. 2006 127 610
14. St.Clair T L., St.Clair A K., Thrasher J S., US 5,220,070 1993, Winter R W., Nixon P G., Gard G L., Castner D G., Holcomb N R., Hu Y.-H, Grainger D W., Chem. Mater. 1999 11 3044
15. Abe T, Tao G.-H, Joo Y.-H, Winter R W., Gard G L., Shreeve J M., Chem. Eur. J. 2009 15 9897
16. Nishino S, Shima H, Omata Y, Oda H, WO 2009,028,514 2009, Kirsch P, Tarumi K, Krause J, DE 19,748,108 1999
17. Brel V K., J. Fluorine Chem. 2007 128 862
18. Brel V K., Synthesis 2005 1245
19. Brel V K., Synthesis 2006 339
20. Case J R., Ray N H., Roberts H L., J. Chem. Soc. 1961 2066
21. At-Mohand S, Dolbier W R. Jr., Org. Lett. 2002 4 3013
22. Dolbier W R. Jr., Mitani A, Xu W, Ghiviriga I, Org. Lett. 2006 8 5573
23. Dolbier W R. Jr., At-Mohand S, Schertz T D., Sergeeva T A., Cradlebaugh J A., Mitani A, Gard G L., Winter R W., Thrasher J S., [nl] J. Fluorine Chem. 2006 127 1302
24. Winter R W., Gard G L., J. Fluorine Chem. 2008 129 1041
25. Lim D S., Ngo S C., Lal S G., Minnich K E., Welch J T., Tetrahedron Lett. 2008 49 5662
26. Ponomarenko M V., Serguchev Y A., Rschenthaler G.-V, J. Fluorine Chem. 2010 131 270
27. Hoover F W., Coffman D D., J. Org. Chem. 1964 29 3567
28. Sergeeva T A., Dolbier W R. Jr., Org. Lett. 2004 6 2417
29. Winter R W., Gard G L., J. Fluorine Chem. 2004 125 549
30. Dolbier W R. Jr., Zheng Z, J. Org. Chem. 2009 74 5626
31. Klauck A, Seppelt K, Angew. Chem., Int. Ed. Engl. 1994 33 93
32. Winter R W., Dodean R, Holmes L, Gard G L., [nl] J. Fluorine Chem. 2004 125 37
33. Cignarella G, Pasqualucci C R., Gallo G G., Testa E, Tetrahedron 1964 20 1057
34. Trushkov I V., Brel V K., Tetrahedron Lett. 2005 46 4777