Quantitative preparation of 3,4-di(methylene)tetrahydrothiophene-1,1- dioxide by Zn-induced 1,4-debromination. A valuable 6-C reactive diene in [4+2] cycloadditions with DMAD and [60]fullerene

RSC Advances

Volumn 2, Issue 32, 2012, Pages 12269-12277

  Markoulides, Marios S ^a   Ioannou, Charalambos P ^a   Manos, Manolis J ^a   Chronakis, Nikos ^a  

^a UNIVERSITY OF CYPRUS   (Cyprus)

Author keywords

[No Author keywords available]

Indexed keywords

18-CROWN-6; [4+2] CYCLOADDITION REACTIONS; [60] FULLERENE; CONVENTIONAL HEATING; CYCLOADDITIONS; CYCLOADDUCTS; DIELS-ALDER; DIENOPHILES; OPTIMUM REACTION CONDITIONS; PHASE TRANSFER CATALYSTS; PRODUCT YIELDS; REFLUXING; ROOM TEMPERATURE; SHORT REACTION TIME; ULTRASONIC IRRADIATION;

ACETONE; CROWN ETHERS; CYCLOADDITION; FULLERENES; IODINE; MICROWAVE IRRADIATION; OLEFINS; POTASSIUM IODIDE; TOLUENE; ZINC;

COMPLEXATION;

EID: 84871061005     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c2ra22502f     Document Type: Article

References (48)

1. W. Albrecht Justus Liebigs Ann. Chem. 1906 348 31 49
2. O. Diels K. Alder Justus Liebigs Ann. Chem. 1928 460 98 122
3. G. Jayamurugan, J.-P. Gisselbrecht, C. Boudon, F. Schoenebeck, W. B. Schweizer, B. Berneta and F. Diederich, Chem. Commun., 2011, 47, 4520-4522
4. R. Meissner X. Garcias S. Mecozzi J. Rebek, Jr. J. Am. Chem. Soc. 1997 119 77 85
5. S. Sarkar E. Bekyarova S. Niyogi R. C. Haddon J. Am. Chem. Soc. 2011 133 3324 3327
6. A. Dag H. Sahin H. Durmaz G. Hizal U. Tunca J. Polym. Sci., Part A: Polym. Chem. 2011 49 886 892
7. W. Sliwa Fullerene Sci. Technol. 1997 5 1133 1175
8. A. Hirsch and M. Brettreich, In Fullerenes-Chemistry and Reactions; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2005
9. H. Imahori Y. Sakata Adv. Mater. 1997 9 537 546
10. H. Imahori Org. Biomol. Chem. 2004 2 1425 1433
11. S. E. Shaheen C. J. Brabec N. S. Sariciftci F. Padinger T. Fromherz J. C. Hummelen Appl. Phys. Lett. 2001 78 841 843
12. P. Hudhomme C. R. Chim. 2006 9 881 891
13. P. Belik A. Gügel J. Spickermann K. Müllen Angew. Chem., Int. Ed. Engl. 1993 32 78 80
14. G.-W. Wang K. Komatsu Y. Murata M. Shiro Nature 1997 387 583 586
15. K. Komatsu G.-W. Wang Y. Murata T. Tanaka K. Fujiwara K. Yamamoto M. Saunders J. Org. Chem. 1998 63 9358 9366
16. S. Lebedkin S. Ballenweg J. Gross R. Taylor W. Krätschmer Tetrahedron Lett. 1995 36 4971 4974
17. A. B. Smith H. Tokuyama R. M. Strongin G. T. Furst W. J. Romanow J. Am. Chem. Soc. 1995 117 9359 9360
18. A. Gromov S. Lebedkin S. Ballenweg A. G. Avent R. Taylor W. Krätschmer Chem. Commun. 1997 209 210
19. N. Dragoe H. Shimotani J. Wang M. Iwaya A. de Bettencourt-Dias A. L. Balch K. Kitazawa J. Am. Chem. Soc. 2001 123 1294 1301
20. Y. Murata A. Han K. Komatsu Tetrahedron Lett. 2003 44 8199 8201
21. K. Fujiwara K. Komatsu Org. Lett. 2002 4 1039 1041
22. C. Zhang S. Chen Z. Xiao Q. Zuo L. Ding Org. Lett. 2012 14 1508 1511
23. T. J. Hingston M. R. Sambrook K. Porfyrakis G. A. D. Briggs Tetrahedron Lett. 2006 47 7413 7415
24. J. L. Charlton M. M. Alauddin Tetrahedron 1987 43 2873 2889
25. S. Kotha P. Khedkar J. Org. Chem. 2009 74 5667 5670
26. S. Kotha A. S. Chavan J. Org. Chem. 2010 75 4319 4322
27. B. M. Trost M. Shimizu J. Am. Chem. Soc. 1982 104 4299 4301
28. A. Hosomi K. Otaka H. Sakurai Tetrahedron Lett. 1986 27 2881 2884
29. F. Monnat P. Vogel Helv. Chim. Acta 2002 85 712 732
30. E. Roversi R. Scopelliti E. Solari R. Estoppey P. Vogel P. Brana B. Menendez J. A. Sordo Chem.-Eur. J. 2002 8 1336 1355
31. P. Dowd J. Am. Chem. Soc. 1970 92 1066 1068
32. S. Sadeh Y. Gaoni Tetrahedron Lett. 1973 14 2365 2368
33. Y. Gaoni S. Sadeh J. Org. Chem. 1980 45 870 881
34. A. C. Cope F. Kagan J. Am. Chem. Soc. 1958 80 5499 5502
35. N. Watanabe N. Kihara T. Takata Org. Lett. 2001 3 3519 3522
36. G. A. Tashbaev L. Yu. Krivehikova I. M. Nasyrov Chem. Heterocycl. Compd. 1992 28 139 141
37. R. W. Alder P. R. Allen L. S. Edwards G. I. Fray K. E. Fuller P. M. Gore N. M. Hext M. H. Perry A. R. Thomas K. S. Turner J. Chem. Soc., Perkin Trans. 1 1994 21 3071 3077
38. T. Suzuki K. Kubomura H. Fuchii H. Takayama J. Chem. Soc., Chem. Commun. 1990 1687 1689
39. K. Ando M. Kankake T. Suzuki H. Takayama J. Chem. Soc., Chem. Commun. 1992 1100 1102
40. T.-S. Chou M.-L. You J. Org. Chem. 1987 52 2224 2226
41. Y. Gaoni Tetrahedron Lett. 1977 18 947 950
42. G. Vassilikogiannakis N. Chronakis M. Orfanopoulos J. Am. Chem. Soc. 1998 120 9911 9920
43. N. Chronakis M. Orfanopoulos Org. Lett. 2001 3 545 548
44. N. Chronakis M. Orfanopoulos Tetrahedron Lett. 2001 42 1201 1204
45. N. Chronakis G. Froudakis M. Orfanopoulos J. Org. Chem. 2002 67 3284 3289
46. O. Grummitt A. L. Endrey J. Am. Chem. Soc. 1960 82 3614 3619
47. R. D. Smith H. E. Simmons Org. Synth. 1973 5 855
48. Vogel's Textbook of Practical Organic Chemistry, Longman Group UK Limited, 5th edn, 1989, ch. 4, pp. 395-469