Novel sulfur-containing amidecrownophanes: synthesis via tandem Claisen rearrangement and an unpredicted mercuration

Tetrahedron Letters

Volumn 49, Issue 23, 2008, Pages 3770-3774

  Seo, Joobeom ^a   Lee, Shim Sung ^a   Gong, Wei Tao ^b   Hiratani, Kazuhisa ^b  

^a Gyeongsang National University   (South Korea)

^b UTSUNOMIYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDECROWNOPHANE DERIVATIVE; CROWN COMPOUND; DIACYL CHLORIDE; DIAMINE SULFIDE; DIHYDROBENZOFURAN DERIVATIVE; HEAVY METAL; MACROCYCLIC COMPOUND; MERCURY DERIVATIVE; SULFUR;

ARTICLE; CLAISEN REARRANGEMENT; CRYSTAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 43049098168     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.013     Document Type: Article

References (27)

1. Tokuhisa H., Nagawa Y., Uzawa H., and Hiratani K. Tetrahedron Lett. 40 (1999) 8007
2. Hiratani K., Uzawa H., Kasuga K., and Kambayashi H. Tetrahedron Lett. 38 (1997) 8993
3. Nagawa Y., Suga J., Hiratani K., Koyama E., and Kanesato M. Chem. Commun. (2005) 749
4. Hiratani K., Keneyama M., Nagawa Y., Koyama E., and Kanesato M. J. Am. Chem. Soc. 126 (2004) 13568
5. Hiratani K., Suga J., Nagawa Y., Houjou H., Tokuhisa H., Numata M., and Watanabe K. Tetrahedron Lett. 43 (2002) 5747
6. Yoshida H., Saigo K., and Hiratani K. Chem. Lett. 29 (2000) 116
7. Gong W.-T., Hiratani K., Oba T., and Ito S. Tetrahedron Lett. 48 (2007) 3073
8. Bronson R.T., Bradshaw J.S., Savage P.B., Fuangswasdi S., Lee S.C., Krakowiak K.E., and Izatt R.M. J. Org. Chem. 66 (2001) 4752
9. Lee S.J., Jung J.H., Seo J., Yoon I., Park K.-M., Lindoy L.F., and Lee S.S. Org. Lett. 8 (2006) 1641
10. Seo J., Song M.R., Lee J.-E., Lee S.Y., Yoon I., Park K.-M., Kim J., Jung J.H., Park S.B., and Lee S.S. Inorg. Chem. 45 (2006) 952
11. Park K.-M., Lee Y.H., Jin Y., Seo J., Yoon I., Lee S.C., Park S.B., Gong M.-S., Seo M.L., and Lee S.S. Supramol. Chem. 16 (2004) 51
12. Vasilescu L.M., Bray D.J., Clegg J.K., Lindoy L.F., Meehan G.V., and Gang W. Dalton Trans. (2006) 5115
13. Shaw J.L., Wolowska J., Collison D., Howard J., Mclnnes E.J.L., Jonathan M., Blake A.J., Wilson C., and Martin S. J. Am. Chem. Soc. 128 (2006) 13827
14. Janzen D.E., Patel K.N., VanDerveer D.G., and Grant G.J. Chem. Commun. 33 (2006) 3540
15. Vetrichelvan M., Lai Y.-H., and Mok K.F. Dalton Trans. (2003) 295
16. Glenny M.W., van de Water L.G.A., Vere J.M., Blake A.J., Wilson C., Reedijik J., and Schröder M. Polyhedron 25 (2006) 599
17. Comba P., Fath A., Kuhner A., and Nuber B. J. Chem. Soc., Dalton Trans. (1997) 1889
18. Yoshida H., Hiratani K., Ogihara T., Kobayashi Y., Kinbara K., and Saigo K. J. Org. Chem. 68 (2003) 5812
19. 3) δ 32.94, 32.98, 39.12, 69.81, 108.05, 117.93, 122.72, 124.93, 126.32, 128.43, 128.47, 129.15, 133.86, 135.49, 138.23, 153.45, 165.19 ppm.
20. Dwyer F.P.J., and Lions F. J. Am. Chem. Soc. 72 (1950) 1545
21. +), 572.1803; Found 572.1802.
22. 2 = 0.0927 [I > 2σ(I)]. CCDC 659069, 659070 and 659071 contain the supplementary crystallographic data for 2a, 2b and 4.
23. +.
24. Adams R., Roman F.K., and Sperry W.N. J. Am. Chem. Soc. 44 (1922) 1781
25. Lethbridge A., Norman R.O.C., and Thomas C.B. J. Chem. Soc., Perkin Trans. 1 (1975) 2465
26. Recently, we have found an amidecrownophane which can also be changed to dihydrobenzofuran-type macrocycle by thermal reaction at 170 °C for 1 h without solvent in quantitative yield (Tetrahedron Lett. 2008, 49, 2268).
27. Hosokawa T., Miyagi S., Murahashi S.-I., and Sonada A. J. Org. Chem. 43 (1978) 719