SCOPUS 정보 검색 플랫폼

Organic Letters

Volumn 10, Issue 11, 2008, Pages 2163-2166

Synthesis and solid-state structure of perfluorophenyl end-capped polyynes

(4) Kendall, Jamie a McDonald, Robert a Ferguson, Michael J a Tykwinski, Rik R a

a UNIVERSITY OF ALBERTA (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 58149477845 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol800583r Document Type: Article

Times cited : (47)

References (49)

1
- 0000156315
- Patrick, C. R.; Prosser, G. S. Nature (London) 1960, 187, 1021-1021.
- (1960) Nature (London) , vol.187 , pp. 1021-1021
- Patrick, C.R.¹ Prosser, G.S.²

2
- 0346307169
- (a) Vanspeybrouck, W.; Herrebout, W. A.; van der Veken, B. J.; Lundell, J.; Perutz, R. N. J. Phys. Chem. B 2003, 107, 13855-13861.
- (2003) J. Phys. Chem. B , vol.107 , pp. 13855-13861
- Vanspeybrouck, W.¹ Herrebout, W.A.² van der Veken, B.J.³ Lundell, J.⁴ Perutz, R.N.⁵

3
- 0038680376
- (b) Pérez-Casas, S.; Hernández-Trujillo, J.; Costas, M. J. Phys. Chem. B 2003, 107, 4167-4174.
- (2003) J. Phys. Chem. B , vol.107 , pp. 4167-4174
- Pérez-Casas, S.¹ Hernández-Trujillo, J.² Costas, M.³

4
- 0000491257
- (c) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598.
- (1993) Acc. Chem. Res , vol.26 , pp. 593-598
- Williams, J.H.¹

5
- 0035528860
- For reviews, see: a
- For reviews, see: (a) Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651-669.
- (2001) J. Chem. Soc., Perkin Trans. 2 , pp. 651-669
- Hunter, C.A.¹ Lawson, K.R.² Perkins, J.³ Urch, C.J.⁴

6
- 0008794026
- (b) Dahl, T. Acta Chem. Scand. 1988, 42, 1-7.
- (1988) Acta Chem. Scand , vol.42 , pp. 1-7
- Dahl, T.¹

7
- 33646910170
- For examples based on acetylenic derivatives, see: a
- For examples based on acetylenic derivatives, see: (a) Shu, L.; Mu, Z.; Fuchs, H.; Chi, L.; Mayor, M. Chem. Commun. 2006, 1862-1863.
- (2006) Chem. Commun , pp. 1862-1863
- Shu, L.¹ Mu, Z.² Fuchs, H.³ Chi, L.⁴ Mayor, M.⁵

8
- 9144229231
- (b) Collings, J. C.; Burke, J. M.; Smith, P. S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Org. Biomol. Chem. 2004, 2, 3172-3178.
- (2004) Org. Biomol. Chem , vol.2 , pp. 3172-3178
- Collings, J.C.¹ Burke, J.M.² Smith, P.S.³ Batsanov, A.S.⁴ Howard, J.A.K.⁵ Marder, T.B.⁶

9
- 33749523244
- (c) Shu, L.; Mayor, M. Chem. Commun. 2006, 4134-4136.
- (2006) Chem. Commun , pp. 4134-4136
- Shu, L.¹ Mayor, M.²

10
- 33646433437
- (d) Taylor, T. J.; Gabbai, F. P. Organometallics 2006, 25, 2143-2147.
- (2006) Organometallics , vol.25 , pp. 2143-2147
- Taylor, T.J.¹ Gabbai, F.P.²

11
- 10744230312
- (e) Smith, C. E.; Smith, P. S.; Thomas, R. L.; Robins, E. G.; Collings, J. C.; Dai, C.; Scott, A. J.; Borwick, S.; Batsanov, A. S.; Watt, S. W.; Clark, S. J.; Viney, C.; Howard, J. A. K.; Clegg, W.; Marder, T. B. J. Mater. Chem. 2004, 14, 413-420.
- (2004) J. Mater. Chem , vol.14 , pp. 413-420
- Smith, C.E.¹ Smith, P.S.² Thomas, R.L.³ Robins, E.G.⁴ Collings, J.C.⁵ Dai, C.⁶ Scott, A.J.⁷ Borwick, S.⁸ Batsanov, A.S.⁹ Watt, S.W.¹⁰ Clark, S.J.¹¹ Viney, C.¹² Howard, J.A.K.¹³ Clegg, W.¹⁴ Marder, T.B.¹⁵

12
- 4544376455
- (f) Watt, S. W.; Dai, C.; Scott, A. J.; Burke, J. M.; Thomas, R. L.; Collings, J. C.; Viney, C.; Clegg, W.; Marder, T. B. Angew. Chem., Int. Ed. 2004, 43, 3061-3063.
- (2004) Angew. Chem., Int. Ed , vol.43 , pp. 3061-3063
- Watt, S.W.¹ Dai, C.² Scott, A.J.³ Burke, J.M.⁴ Thomas, R.L.⁵ Collings, J.C.⁶ Viney, C.⁷ Clegg, W.⁸ Marder, T.B.⁹

13
- 0041785390
- (g) Gdaniec, M.; Jankowski, W.; Milewska, M. J.; Polonski, T. Angew. Chem., Int. Ed. 2003, 42, 3903-3906.
- (2003) Angew. Chem., Int. Ed , vol.42 , pp. 3903-3906
- Gdaniec, M.¹ Jankowski, W.² Milewska, M.J.³ Polonski, T.⁴

14
- 33646451695
- (h) Xu, R.; Gramlich, V.; Frauenrath, H. J. Am. Chem. Soc. 2006, 128, 5541-5547.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 5541-5547
- Xu, R.¹ Gramlich, V.² Frauenrath, H.³

15
- 0031001589
- Coates, G. W.; Dunn, A. R.; Henling, L. M.; Dougherty, D. A.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 248-251.
- (1997) Angew. Chem., Int. Ed. Engl , vol.36 , pp. 248-251
- Coates, G.W.¹ Dunn, A.R.² Henling, L.M.³ Dougherty, D.A.⁴ Grubbs, R.H.⁵

16
- 0345549642
- For a description of such reactions, see
- For a description of such reactions, see: Szafert, S.; Gladysz, J. A. Chem. ReV. 2003, 103, 4175-4205.
- Chem. Re , vol.2003 , Issue.103 , pp. 4175-4205
- Szafert, S.¹ Gladysz, J.A.²

17
- 33748535410
- For recent examples of polyyne formation using the FBW rearrangement, see: a
- For recent examples of polyyne formation using the FBW rearrangement, see: (a) Chalifoux, W. A.; Tykwinski, R. R. Chem. Rec. 2006, 6, 169-182.
- (2006) Chem. Rec , vol.6 , pp. 169-182
- Chalifoux, W.A.¹ Tykwinski, R.R.²

18
- 12344269243
- (b) Luu, T.; Elliott, E.; Slepkov, A. D.; Eisler, S.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. Org. Lett. 2005, 7, 51-54.
- (2005) Org. Lett , vol.7 , pp. 51-54
- Luu, T.¹ Elliott, E.² Slepkov, A.D.³ Eisler, S.⁴ McDonald, R.⁵ Hegmann, F.A.⁶ Tykwinski, R.R.⁷

19
- 14744270102
- (c) Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.; Hegmann, F. A.; Tywkinski, R. R. J. Am. Chem. Soc. 2005, 127, 2666-2676.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 2666-2676
- Eisler, S.¹ Slepkov, A.D.² Elliott, E.³ Luu, T.⁴ McDonald, R.⁵ Hegmann, F.A.⁶ Tywkinski, R.R.⁷

20
- 84891029339
- Diederich, F, Stang, P. J, Tykwinski, R. R, Eds, Wiley-VCH: Weinheim, Germany
- (d) Eisler, S.; Tykwinski, R. R. In Acetylene Chemistry: Chemistry, Biology, and Material Science; Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
- (2005) Acetylene Chemistry: Chemistry, Biology, and Material Science
- Eisler, S.¹ Tykwinski, R.R.²

21
- 0038312023
- (e) Eisler, S.; Chahal, N.; McDonald, R.; Tykwinski, R. R. Chem. Eur. J. 2003, 9, 2542-2550.
- (2003) Chem. Eur. J , vol.9 , pp. 2542-2550
- Eisler, S.¹ Chahal, N.² McDonald, R.³ Tykwinski, R.R.⁴

22
- 85082556031
- Zhang, Y.; Wen, J. Synthesis 1990, 727-728.
- (1990) Synthesis , pp. 727-728
- Zhang, Y.¹ Wen, J.²

23
- 0009505403
- (a) Fritsch, P. Liebigs Ann. Chem. 1894, 279, 319-323.
- (1894) Liebigs Ann. Chem , vol.279 , pp. 319-323
- Fritsch, P.¹

24
- 0009545744
- (b) Buttenberg, W. P. Liebigs Ann. Chem. 1894, 279, 324-337.
- (1894) Liebigs Ann. Chem , vol.279 , pp. 324-337
- Buttenberg, W.P.¹

25
- 0009545745
- (c) Wiechell, H. Liebigs Ann. Chem. 1894, 279, 337-344.
- (1894) Liebigs Ann. Chem , vol.279 , pp. 337-344
- Wiechell, H.¹

26
- 4644275985
- For a recent review, see
- (d) For a recent review, see: Knorr, R. Chem. Rev. 2004, 104, 3795-3849.
- (2004) Chem. Rev , vol.104 , pp. 3795-3849
- Knorr, R.¹

27
- 0002269581
- Walton, D. R. M.; Waugh, F. J. Organomet. Chem. 1972, 37, 45-56.
- (1972) J. Organomet. Chem , vol.37 , pp. 45-56
- Walton, D.R.M.¹ Waugh, F.²

28
- 37049079344
- Chen, Q.-Y.; Li, Z.-T. J. Chem. Soc., Perkin Trans. 1 1992, 2931-2934.
- (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 2931-2934
- Chen, Q.-Y.¹ Li, Z.-T.²

29
- 37049109989
- Colvin, E. W.; Hamill, B. J. J. Chem. Soc., Perkin Trans. 1 1977, 869-874.
- (1977) J. Chem. Soc., Perkin Trans. 1 , pp. 869-874
- Colvin, E.W.¹ Hamill, B.J.²

30
- 59849124805
- See Supporting Information for details
- See Supporting Information for details.

31
- 0004294109
- Viehe, H. G, Ed, Marcel Dekker: New York
- Cadiot, P.; Chodkiewicz, W. In Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; pp 597-647.
- (1969) Chemistry of Acetylenes , pp. 597-647
- Cadiot, P.¹ Chodkiewicz, W.²

32
- 36148956166
- For recent examples of polyyne formation using the Cadiot-Chodkiewicz method, see
- For recent examples of polyyne formation using the Cadiot-Chodkiewicz method, see: Lee, S.; Lee, T.; Lee, Y. M.; Kim, D.; Kim, S. Angew Chem., Int. Ed. 2007, 46, 8422-8425.
- (2007) Angew Chem., Int. Ed , vol.46 , pp. 8422-8425
- Lee, S.¹ Lee, T.² Lee, Y.M.³ Kim, D.⁴ Kim, S.⁵

33
- 33646789860
- (c) Sabitha, G.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2006, 47, 4513-4516.
- (2006) Tetrahedron Lett , vol.47 , pp. 4513-4516
- Sabitha, G.¹ Reddy, C.S.² Yadav, J.S.³

34
- 0038711345
- (d) Gung, B. W.; Kumi, G. J. Org. Chem. 2003, 68, 5956-5960.
- (2003) J. Org. Chem , vol.68 , pp. 5956-5960
- Gung, B.W.¹ Kumi, G.²

35
- 33947476790
- Hay, A. S. J. Org. Chem. 1962, 27, 3320-3321.
- (1962) J. Org. Chem , vol.27 , pp. 3320-3321
- Hay, A.S.¹

36
- 34447123922
- For recent examples of polyyne formation using the Hay and similar methods, see
- For recent examples of polyyne formation using the Hay and similar methods, see: de Quadras, L.; Bauer, E. B.; Mohr, W.; Bohling, J. C.; Peters, T. B.; Martín-Alvarez, J. M.; Hampel, F.; Gladysz, J. A. J. Am. Chem. Soc. 2007, 129, 8296-8309.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 8296-8309
- de Quadras, L.¹ Bauer, E.B.² Mohr, W.³ Bohling, J.C.⁴ Peters, T.B.⁵ Martín-Alvarez, J.M.⁶ Hampel, F.⁷ Gladysz, J.A.⁸

37
- 34948820159
- Simpkins, S. M. E.; Weller, M. D.; Cox, L. R. Chem. Commun. 2007, 4035-4037.
- (2007) Chem. Commun , pp. 4035-4037
- Simpkins, S.M.E.¹ Weller, M.D.² Cox, L.R.³

38
- 33748571531
- Zheng, Q.; Bohling, J. C.; Peters, T. B.; Frisch, A. C.; Hampel, F.; Gladysz, J. A. Chem. Eur. J. 2006, 12, 6486-6505.
- (2006) Chem. Eur. J , vol.12 , pp. 6486-6505
- Zheng, Q.¹ Bohling, J.C.² Peters, T.B.³ Frisch, A.C.⁴ Hampel, F.⁵ Gladysz, J.A.⁶

39
- 0037127074
- Gibtner, T.; Hampel, F.; Gisselbrecht, J.-P.; Hirsch, A. Chem. Eur. J. 2002, 8, 408-432.
- (2002) Chem. Eur. J , vol.8 , pp. 408-432
- Gibtner, T.¹ Hampel, F.² Gisselbrecht, J.-P.³ Hirsch, A.⁴

40
- 33947473632
- (a) Ramirez, F.; Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745-1747.
- (1962) J. Am. Chem. Soc , vol.84 , pp. 1745-1747
- Ramirez, F.¹ Desai, N.B.² McKelvie, N.³

41
- 0000344537
- (b) Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
- (1972) Tetrahedron Lett , pp. 3769-3772
- Corey, E.J.¹ Fuchs, P.L.²

42
- 33646120606
- Rubin, Y.; Lin, S. S.; Knobler, C. B.; Anthony, J.; Boldi, A. M.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 6943-6949.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 6943-6949
- Rubin, Y.¹ Lin, S.S.² Knobler, C.B.³ Anthony, J.⁴ Boldi, A.M.⁵ Diederich, F.⁶

43
- 37049128994
- Birchall, J. M.; Bowden, F. L.; Haszeldine, R. N.; Lever, A. B. P. J. Chem. Soc. A 1967, 747-753.
- (1967) J. Chem. Soc. A , pp. 747-753
- Birchall, J.M.¹ Bowden, F.L.² Haszeldine, R.N.³ Lever, A.B.P.⁴

44
- 37049044649
- Armitage, J. B.; Entwistle, N.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1954, 147-154.
- (1954) J. Chem. Soc , pp. 147-154
- Armitage, J.B.¹ Entwistle, N.² Jones, E.R.H.³ Whiting, M.C.⁴

45
- 59849109434
- X-ray crystallographic data for 7: C18H 5F5, M, 316.22, triclinic space group P1 (No. 2, a, 7.3722(6) Å, b, 7.9609(10) Å, c, 13.2604 (12) Å; α, 101.447(9)°, β, 91.357(7)°, γ, 114.541(7)°; V, 688.93(12) Å3; Z, 2; ρcalcd, 1.524 g cm-3, μ, 0.136 mm -1; T, 80 ° C. Final R1, 0.0453 (1881 observations [Fo2 ≥ 2σ(F o2), wR2, 0.1266 for 209 variables and 2838 data with [Fo2 ≥, 3σFo2, CCDC 677133
- 2)]; CCDC 677133.

46
- 59849114920
- Intermolecular distances are based on the separation of planes generated from all non-hydrogen atoms of neighboring molecules using Mercury 1.3; see the Supporting Information for more details
- Intermolecular distances are based on the separation of planes generated from all non-hydrogen atoms of neighboring molecules using Mercury 1.3; see the Supporting Information for more details.

47
- 59849101333
- X-ray crystallographic data for 12: C20H 5F5, M, 340.24; triclinic space group P1 (No. 2, ρc, 1.470 g cm-3; a, 7.3896(12) Å, b, 7.9448(13) Å, c, 14.452(2) Å; α, 91.906(3)°, β, 94.375(3)°, γ, 114.390(2)°; V, 768.5(2) Å3; Z, 2; μ, 0.128 mm-1. Final R(F, 0.0710 (1522 observations [Fo2 ≥ 2σ(Fo2), wR2, 0.2125 for 226 variables and 2702 data with [Fo2 ≥ -3σFo2, CCDC 677134
- 2)]; CCDC 677134.

48
- 0030812228
- Haley, M. M.; Bell, M. L.; Brand, S. C.; Kimball, D. B.; Pak, J. J.; Wan, W. B. Tetrahedron Lett. 1997, 38, 7483-7486.
- (1997) Tetrahedron Lett , vol.38 , pp. 7483-7486
- Haley, M.M.¹ Bell, M.L.² Brand, S.C.³ Kimball, D.B.⁴ Pak, J.J.⁵ Wan, W.B.⁶

49
- 59849117742
- X-ray crystallographic data for 16·25: C40H 10F10, M, 680.48; triclinic space group P1 (No. 2, ρc, 1.483 g cm-3; a, 7.3625(10) Å, b, 7.8987(11) Å, c, 14.684(2) Å; α, 82.017(2)°, β, 80.119(2)°, γ, 65.267(2)°; V, 761.97(18) Å3; Z, 1; μ, 0.129 mm-1. Final R(F, 0.0413 (1910 observations [Fo2 ≥ 2σ(Fo2), wR2, 0.1386 for 226 variables and 2969 data with [Fo2 ≥ -3σFo2, CCDC 677135
- 2)]; CCDC 677135.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.