Synthesis and spectroscopic study of silacyclyne-substituted phenyleneethynylenes

Tetrahedron Letters

Volumn 50, Issue 24, 2009, Pages 2860-2864

  Mao, Guoliang ^a   Orita, Akihiro ^a   Matsuo, Daisuke ^a   Hirate, Takayoshi ^a   Iwanaga, Tetsuo ^a   Toyota, Shinji ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Aldehydes; Alkynes; Eliminations; Silacyclynes; Sulfones

Indexed keywords

ALKYNE DERIVATIVE; BENZENE DERIVATIVE; SILACYCLYNE PHENYLENEETHYNYLENE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEPROTECTION REACTION; SANDMEYER REACTION; SONOGASHIRA REACTION; SPECTROSCOPY; SYNTHESIS;

EID: 65249150243     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.163     Document Type: Article

References (34)

1. For recent reviews on dehydrobenzoannulenes:. Tobe Y., and Sonoda M. In: Gleiter R., and Hopf H. (Eds). Modern Cyclophane Chemistry (2004), Wiley-VCH, Weinheim, Germany 1
2. Jones C.S., O'Connor M.J., and Haley M.M. In: Diederich F., Stang P.J., and Tykwinski R.R. (Eds). Acetylene Chemistry: Chemistry, Biology and Material Science (2005), Wiley-VCH, Weinheim, Germany 303
3. Spitler E.L., Johnson II C.A., and Haley M.M. Chem. Rev. 106 (2006) 5344
4. Ferrara J.D., Tessier-Youngs C., and Youngs W.J. J. Am. Chen. Soc. 110 (1988) 3326
5. Ferrara J.D., Tanaka A., Fierro C., Tessier-Youngs C., and Youngs W.J. Organometallics 8 (1989) 2089
6. Pu Y.-J., Takahashi M., Tsuchida E., and Nishide H. Mol. Cryst. Liq. Cryst. 334 (1999) 1
7. Pu Y.-J., Takahashi M., Tsuchida E., and Nishide H. Chem. Lett. (1999) 161
8. Sonoda M., Sakai Y., Yoshimura T., Tobe Y., and Kamada K. Chem. Lett. 33 (2004) 972
9. Sarkar A., Pak J.J., Rayfield G.W., and Haley M.M. J. Mater. Chem. 11 (2001) 2943
10. Tahara K., Yoshimura T., Ohno M., Sonoda M., and Tobe Y. Chem. Lett. 36 (2007) 838
11. For recent reviews:. Marsden J.A., Palmer G.J., and Haley M.M. Eur. J. Org. Chem. (2003) 2355
12. Haley M.M. Synlett (1998) 557
13. Haley M.M., and Wan W.B. In: Halton B. (Ed). Advances in Strained and Interesting Organic Molecules Vol. 8 (2000), JAI Press, New York 1
14. Bunz U.H.F., Rubin Y., and Tobe Y. Chem. Soc. Rev. 28 (1999) 107
15. Hertel D., and Bässler H. In: Müllen K., and Scherf U. (Eds). Organic Light-Emitting Devices: Synthesis, Properties, and Applications (2006), Wiley-VCH, Weinheim, Germany 95
16. It has been reported that a fluorescence quantum yield of dehydrobenzo[12]annulene is 0.15:. Janecka-Styrcz K., Lipinski J., and Ruziewicz Z. J. Lumin. 17 (1978) 83 For substituted dehydrobenzo[12]annulenes, fluorescence quantum yields are 0.08 and 0.06: see Ref. 2e
17. Otera J. Pure Appl. Chem. 78 (2006) 731
18. Orita A., and Otera J. Chem. Rev. 106 (2006) 5387
19. Doi T., Orita A., Matsuo D., Saijo R., and Otera J. Synlett (2008) 55
20. Ding C., Babu G., Orita A., Hirate T., and Otera J. Synlett (2007) 2559
21. An D.-L., Zhang Z., Orita A., Mineyama H., and Otera J. Synlett (2007) 1909
22. Shao G., Orita A., Taniguchi H., Ishimaru K., and Otera J. Synlett (2007) 231
23. Shao G., Orita A., Nishijima K., Ishimaru K., Takezaki M., Wakamatsu K., Gleiter R., and Otera J. Chem. Asian J. 2 (2007) 489
24. Shao G., Orita A., Nishijima K., Ishimaru K., Takezaki M., Wakamatsu K., and Otera J. Chem. Lett. 35 (2006) 1284
25. Tahara K., Yoshimura T., Sonoda M., Tobe Y., and Williams R.V. J. Org. Chem. 72 (2007) 1437
26. Kamada K., Antonov L., Yamada S., Ohta K., Yoshimura T., Tahara K., Inaba A., Sonoda M., and Tobe Y. ChemPhysChem 8 (2007) 2671
27. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. (1975) 4467
28. Tohda Y., Sonogashira K., and Hagihara N. Synthesis (1977) 777
29. Takahashi S., Kuroyama Y., Sonogashira K., and Hagihara N. Synthesis (1980) 627
30. For a most recent review:. Chinchilla R., and Nájera C. Chem. Rev. 107 (2007) 874
31. 6 and nickel(0) have been already reported:. Guo L., Brandshaw J.D., McConville D.B., Tessier C.A., and Youngs W.J. Organometallics 16 (1997) 1685
32. Guo L., Brandshaw J.D., Tessier C.A., and Youngs W.J. Organometallics 14 (1995) 586
33. Syntheses of silacyclynes 1c-f were fully described in Supplementary data.
34. Aggregation of π-conjugated material induces a low fluorescence quantum yield. Joswick M.D., Cambell I.H., Barashkov N.N., and Ferraris J.P.J. Appl. Phys. 80 (1996) 2883