Oxa-bridged cyclophanes featuring thieno[2,3-b]thiophene and C2-symmetric binol or bis-naphthol rings: synthesis, structures, and conformational studies

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8837-8842

  Mashraqui, Sabir H ^a   Sangvikar, Yogesh S ^a   Ghadigaonkar, Shailesh G ^a   Ashraf, Mohamed ^a   Meetsma, M ^b  

^a UNIVERSITY OF MUMBAI   (India)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CYCLOPHANE DERIVATIVE; NAPHTHOL DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; HIGH TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 48149101258     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.076     Document Type: Article

References (63)

1. Eliel E.L., and Wilen S.H. Stereochemistry of Organic Compound (1994), John Wiley & Sons, New York, NY
2. In: Ager D.J., and East M.B. (Eds). Asymmetric Synthetic Methodology (1996), CRC, Boca Raton, FL
3. Lehn J.-M. Supramolecular Chmistry. Concepts and Perspectives (1995), VCH, Weinheim
4. Gibson S.E., and Knight J.D. Org. Biomol. Chem. 1 (2003) 1256-1269
5. Ernst L. Prog. Nucl. Magn. Reson. Spectrosc. 37 (2000) 47-190
6. Iwanaga T., Nakamoto R., Yasutake M., Takemura H., Sako K., and Shinmyozu T. Angew. Chem., Int. Ed. 45 (2006) 3643-3647
7. Ueda T., Kanomata N., and Machida H. Org. Lett. 7 (2005) 2365-2368
8. Butler D.N., Shang M., and Warrener R.N. Tetrahedron Lett. 41 (2000) 5985-5989
9. Bazan G.C., Zyss J., Bartholomew G.P., Ledoux I., and Mukamel S. J. Am. Chem. Soc. 124 (2002) 13480-13485
10. Grimme S. Chem.-Eur. J. 19 (2004) 3423-3429
11. Losensky H.-W., Spelthann H., Ehlen A., Vögtle F., and Bargon J. Angew. Chem., Int. Ed. Engl. 27 (1988) 1189-1191
12. Grimme S., Hareen J., Sobanski A., and Vogtle F. Eur. J. Org. Chem. (1998) 1491-1509
13. Alcalde E., Ramos S., and Perez-Garcia L. Org. Lett. 1 (1999) 1035-1038
14. Camacho D.H., Salo E.V., and Guan Z. Org. Lett. 6 (2004) 865-868
15. Isabel Burguete M., Diaz P., Gracia-Espana E., Luis S.V., Miravet J.F., Querol M., and Ramirez J.A. Chem. Commun. (1999) 649-650
16. In: Keehn P.M., and Rosenfeld S.M. (Eds). Cyclophanes Vols. I and II (1983), Academic, New York, NY
17. Diederich F. Cyclophane (1991), Royal Society of Chemistry, Cambridge
18. Vogtle F. Cyclophane Chemistry (1993), Wiley-VCH, Chichester
19. In: Gleiter R., and Hopf H. (Eds). Modern Cyclophane Chemistry (2004), Wiley-VCH, Weinheim
20. Oki M. In: Marchand A.P. (Ed). Applications of Dynamic NMR Spectroscopy to Organic Chemistry. Methods of Stereochemical Analysis Vol. 4 (1985), VCH, Deerfield Beach, Florida, FL p 234
21. Mitchell R.H. In: Keehn P.M., and Rosenfeld S.M. (Eds). Cyclophanes Vol. 1 (1983), Academic, New York, NY p 239
22. Aly A.A., Hopf H., and Ernst L. Eur. J. Org. Chem. (2000) 3021-3029
23. Paudler W.W., and Bezoari M.D. In: Keehn P.M., and Rosenfeld S.M. (Eds). Cyclophanes Vol. 2 (1983), Academic, New York, NY 359-441
24. Seyama F., Akahori K., Sakata Y., Misum S., Aida M., and Nagata C. J. Am. Chem. Soc. 110 (1988) 2192-2201
25. Akahori K., Hama F., Sakata Y., and Misum S. Tetrahedron Lett. 25 (1984) 2379-2384
26. Zipplies M.F., and Staab H.A. Tetrahedron Lett. 25 (1984) 1035-1037
27. Hamilton A.D., and Pant N. J. Chem. Soc., Chem. Commun. (1988) 765-766
28. Cram D.J., Helgeson R.C., Sousa L.R., Timko J.M., Newcomb M., Moreau P., De Jong F., Gokel G.W., and Hofmann D.H. Pure Appl. Chem. 43 (1975) 327-349
29. Zhang X.X., Bradshaw J.S., and Izatt R.M. Chem. Rev. 97 (1997) 3313-3362
30. Thijs Stock H., and Kellogg R.M. J. Org. Chem. 61 (1996) 3093-3105
31. Brunner H., and Schiessling H. Angew. Chem., Int. Ed. Engl. 33 (1994) 125-126
32. Lin J., Zhang H.-C., and Pu L. Org. Lett. 4 (2002) 3297-3300
33. Miyano S., Handa S., Shimizu K., Tagami K., and Hashomoto H. Bull. Chem. Soc. Jpn. 57 (1984) 1943-1947
34. Smith R.A.J., Hanton L., and Bandarage U.K. Synth. Commun. 25 (1995) 3845-3854
35. Diederich F., Hester M.R., and Uyeki M.A. Angew. Chem. 100 (1988) 1775-1777
36. Yang D., Wang X.-C., Wong M.K., Yip Y.C., and Tang M.W. J. Am. Chem. Soc. 118 (1996) 11311-11312
37. Mazaleyrat J.-P., and Waklesman M. J. Org. Chem. 61 (1996) 2695-2698
38. Kakuchi T., and Yokota Y. Macromol. Rapid Commun. 8 (2003) 551-555
39. Murahashi S.-I., Noji S., and Komiya N. Adv. Synth. Catal. 346 (2004) 195-198
40. Rajakumar P., and Srisailas. Tetrahedron 57 (2001) 9749-9754
41. Lee S.J., and Wenbin L. Encyclopedia of Nanoscience and Nanotechnology Vol. I (2004) 863-875
42. Barnes J.C., Paton J.D., Damewood Jr. J.R., and Mislow K. J. Org. Chem. 46 (1981) 4975-4979
43. Saigo K., Kihara N., Hashimoto Y., Lin R.-J., Fujimura H., Suzuki Y., and Hasegawa M. J. Am. Chem. Soc. 112 (1990) 1144-1150
44. Chang S.K., and Hamilton A.D. J. Am. Chem. Soc. 110 (1988) 1318-1319
45. Lockhart J.C., McDonald M.B., and Tyson P.D. J. Chem. Soc., Perkin Trans. 1 (1983) 2153-2159
46. Mashraqui S.H., and Kumar S. Indian J. Chem. B 37 (1998) 348-351
47. Litinov V.P. Russ. Chem. Rev. 74 (2005) 217-248
48. Mashraqui S.H., Ashraf M., Hariharasubrahmanian H., Kellogg R.M., and Meetsma M. J. Mol. Struct. 689 (2004) 107-113
49. Mashraqui S.H., Hariharasubramanian H., Ashraf M., and Sangvikar Y. Indian J. Chem. B 44 (2005) 115-120
50. Mashraqui S.H., Sangvikar Y., Ashraf M., Kumar S., and daub E.T.H. Tetrahedron 61 (2005) 3507-3513
51. Martin H., Clare B., Kristijonas G., Maxim S., David S., Tierney S., and McCulloch I. J. Am. Chem. Soc. 127 (2005) 1078-1079
52. Hayashi N., Mazaki Y., and Kobayashi K. J. Chem. Soc., Chem. Commun. (1994) 2351-2352
53. Sato N., Mazaki Y., Kobayhashi K., and Kobayhashi T. J. Chem. Soc., Perkin Trans. 2 (1992) 765-770
54. Mashraqui S.H., Ghadigaonkar S., Ashraf M., Sri Ranjini A., Ghosh S., and Das P.K. Tetrahedron 63 (2007) 10011-10017
55. Mashraqui S.H., Sangvikar Y.S., and Meetsma A. Tetrahedron Lett. 47 (2006) 5599-5602
56. Mashraqui S.H., Hariharasubramanian H., and Kumar S. Synthesis 12 (1999) 2030-2032
57. Rate of inversion (K) and Arrhenius energy of activation (ΔG) were calculated as per the equations given in the paper:. Akabori S., Hayashi S., Nawa M., and Shiomi K. Tetrahedron Lett. (1969) 3727-3728
58. Lai Y.-H., Wong S.-Y., and Change D.H.-Y. Tetrahedron 49 (1993) 669-676
59. Lai Y.-H., Ang S.-G., and Wong S.-Y. Tetrahedron Lett. 38 (1997) 2553-2556
60. Beurskens P.T., Beurskens G., De Gelder R., Garcia-Granda S., Gould R., Israel O.R., and Smits J.M.M. The DIRDIF-99 Program System, Crystallography Laboratory (1999), University of Nijmegen, The Netherlands
61. Sheldrick G.M. SHELXL-97. Program for the Refinement of Crystal Structures (1997), University of Gottingen, Germany
62. The X-ray crystal structure data have been submitted to the Cambridge Data-base as a file CCDC-297142.
63. Akimoto H., Shioiri T., Itaka Y., and Yamad S.-I. Tetrahedron Lett. 9 (1968) 97-102