SCOPUS 정보 검색 플랫폼

Volumn , Issue 20, 2008, Pages 3153-3156

Novel synthetic route to dihydropyrenes

(8) Chifuku, Kazufumi a Sawada, Tsuyoshi a Kihara, Takao a Shimojo, Kentaro a Sonoda, Hidetoshi a Kuwahara, Yutaka a Shosenji, Hideto a Ihara, Hirotaka a

a KUMAMOTO UNIVERSITY (Japan)

Author keywords

Arenes; Cyclophanes; Oxidations; Photochemistry; Reduction

Indexed keywords

EID: 58149361397 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1087363 Document Type: Article

Times cited : (6)

References (25)

1
- 0000990011
- Boekelheide, V.; Phillips, J. B. J. Am. Chem. Soc. 1967, 89, 1695.
- (1967) J. Am. Chem. Soc , vol.89 , pp. 1695
- Boekelheide, V.¹ Phillips, J.B.²

2
- 39149114396
- (a) Zhao, P.; Fang, C.; Xia, C.; Liu, D.; Xie, S. Chem. Phys. Lett. 2008, 453, 62.
- (2008) Chem. Phys. Lett , vol.453 , pp. 62
- Zhao, P.¹ Fang, C.² Xia, C.³ Liu, D.⁴ Xie, S.⁵

3
- 33846684922
- (b) Andreasson, J.; Straight, S. D.; Bandyopadhyay, S.; Mitchell, R. H.; Moore, T. A.; Moore, A. L.; Gust, D. Angew. Chem. Int. Ed. 2007, 46, 958.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 958
- Andreasson, J.¹ Straight, S.D.² Bandyopadhyay, S.³ Mitchell, R.H.⁴ Moore, T.A.⁵ Moore, A.L.⁶ Gust, D.⁷

4
- 34547585981
- (c) Lee, H.; Robinson, S. G.; Bandyopadhyay, S.; Mitchell, R. H.; Sen, D. J. Mol. Biol. 2007, 371, 1163.
- (2007) J. Mol. Biol , vol.371 , pp. 1163
- Lee, H.¹ Robinson, S.G.² Bandyopadhyay, S.³ Mitchell, R.H.⁴ Sen, D.⁵

5
- 21644466236
- (d) Straight, A. D.; Andreasson, J.; Kodis, G.; Bandyopadhyay, S.; Mitchell, R. H.; Moore, T. A.; Moore, A. L.; Gust, D. J. Am. Chem. Soc. 2005, 127, 9403.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 9403
- Straight, A.D.¹ Andreasson, J.² Kodis, G.³ Bandyopadhyay, S.⁴ Mitchell, R.H.⁵ Moore, T.A.⁶ Moore, A.L.⁷ Gust, D.⁸

6
- 1942439825
- (e) Liddell, P. A.; Kodis, G.; Andreasson, J.; Garza, L. D. L.; Bandyopadhyay, S.; Mitchell, R. H.; Moore, T. A.; Moore, A. L.; Gust, D. J. Am. Chem. Soc. 2004, 126, 4803.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 4803
- Liddell, P.A.¹ Kodis, G.² Andreasson, J.³ Garza, L.D.L.⁴ Bandyopadhyay, S.⁵ Mitchell, R.H.⁶ Moore, T.A.⁷ Moore, A.L.⁸ Gust, D.⁹

7
- 0000673533
- (f) Marsella, M. J.; Wang, Z.; Mitchell, R. H. Org. Lett. 2000, 2, 2979.
- (2000) Org. Lett , vol.2 , pp. 2979
- Marsella, M.J.¹ Wang, Z.² Mitchell, R.H.³

8
- 0001027370
- Tashiro, M.; Yamato, T. J. Am. Chem. Soc. 1982, 104, 3701.
- (1982) J. Am. Chem. Soc , vol.104 , pp. 3701
- Tashiro, M.¹ Yamato, T.²

9
- 0037433514
- Mitchell, R. H.; Ward, T. R.; Chen, Y.; Wang, Y.; Weerawarna, S. A.; Dibble, P. W.; Marsella, M. J.; Almutairi, A.; Wang, Z. J. Am. Chem. Soc. 2003, 125, 2974.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 2974
- Mitchell, R.H.¹ Ward, T.R.² Chen, Y.³ Wang, Y.⁴ Weerawarna, S.A.⁵ Dibble, P.W.⁶ Marsella, M.J.⁷ Almutairi, A.⁸ Wang, Z.⁹

10
- 0033605197
- (a) Sahade, D. A.; Tsukamoto, K.; Thiemann, T.; Sawada, T.; Mataka, S. Tetrahedron 1999, 55, 2573.
- (1999) Tetrahedron , vol.55 , pp. 2573
- Sahade, D.A.¹ Tsukamoto, K.² Thiemann, T.³ Sawada, T.⁴ Mataka, S.⁵

11
- 0030952729
- (b) Sahade, D. A.; Mataka, S.; Sawada, T.; Tsukinoki, T.; Tashiro, M. Tetrahedron Lett. 1997, 38, 3745.
- (1997) Tetrahedron Lett , vol.38 , pp. 3745
- Sahade, D.A.¹ Mataka, S.² Sawada, T.³ Tsukinoki, T.⁴ Tashiro, M.⁵

12
- 0038561203
- Sheepwash, M. A. L.; Ward, T. R.; Wang, Y.; Bandyopadhyay, S.; Mitchell, R. H.; Bohne, C. Photochem. Photobiol. Sci. 2003, 2, 104.
- (2003) Photochem. Photobiol. Sci , vol.2 , pp. 104
- Sheepwash, M.A.L.¹ Ward, T.R.² Wang, Y.³ Bandyopadhyay, S.⁴ Mitchell, R.H.⁵ Bohne, C.⁶

13
- 0001459506
- Zhengchun, L.; Classon, B. J. Org. Chem. 1990, 55, 4273.
- (1990) J. Org. Chem , vol.55 , pp. 4273
- Zhengchun, L.¹ Classon, B.²

14
- 58149341474
- Synthesis of 3 from 6 To a stirred suspension of 6 (100 mg, 0.24 mmol, imidazole (196 mg, 2.88 mmol, and chlorodiphenylphosphine (235 mg, 1.00 mol) in toluene (50 mL) was added iodine (243 mg, 1.00 mmol) portionwise at reflux temperature, and the mixture was refluxed for 1 h. Zinc powder (667 mg, 9.76 mmol) was added, and the mixture was refluxed for 8 h. The mixture was cooled to r.t. and washed with 1 M NaOH (50 mL, H2O (50 mL, and brine. The organic layer was dried over MgSO4, evaporated in vacuo, and purified by TLC to afford 3 (63 mg, 75, and 7 (8 mg, 7, as green powders. Compound 3: mp (from n-hexane) 201-203°C (lit.4 mp 203-204°C, 1H NMR (400 MHz, 25°C, CDCl3, δ, 4.04 (s, 6 H, 1.69 (s, 18 H, 8.46 (s, 4 H, 8.54 (s, 4 H, Compound 7: mp (from n-hexane) 104-105°C. FT-IR: 697, 732, 1026, 1109, 1130, 1161, 1236, 1360, 1437, 2861, 2906, 2926
- + + Na].

15
- 84985702456
- Garegg, P. J.; Samuelsson, B. Synthesis 1979, 469.
- (1979) Synthesis , pp. 469
- Garegg, P.J.¹ Samuelsson, B.²

16
- 33746894578
- Fox, D. J.; Pedersen, D. S.; Petersen, A. B.; Warren, S. Org. Biomol. Chem. 2006, 4, 3117.
- (2006) Org. Biomol. Chem , vol.4 , pp. 3117
- Fox, D.J.¹ Pedersen, D.S.² Petersen, A.B.³ Warren, S.⁴

17
- 0033580875
- Tsukamoto, K.; Sahade, D. A.; Taniguchi, M.; Sawada, T.; Thiemann, T.; Mataka, S. Tetrahedron Lett. 1999, 40, 4691.
- (1999) Tetrahedron Lett , vol.40 , pp. 4691
- Tsukamoto, K.¹ Sahade, D.A.² Taniguchi, M.³ Sawada, T.⁴ Thiemann, T.⁵ Mataka, S.⁶

18
- 33947338336
- Albright, J. D.; Goldman, L. J. Am. Chem. Soc. 1967, 89, 2416.
- (1967) J. Am. Chem. Soc , vol.89 , pp. 2416
- Albright, J.D.¹ Goldman, L.²

19
- 58149355666
- 3): δ = 0.89 (s, 6 H), 1.29 (s, 18 H), 7.58 (s, 4 H).
- 3): δ = 0.89 (s, 6 H), 1.29 (s, 18 H), 7.58 (s, 4 H).

20
- 0035814415
- (a) Phillips, K. E. S.; Katz, T. J.; Jockusch, S.; Lovinger, A. J.; Turro, N. J. J. Am. Chem. Soc. 2001, 123, 11899.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 11899
- Phillips, K.E.S.¹ Katz, T.J.² Jockusch, S.³ Lovinger, A.J.⁴ Turro, N.J.⁵

21
- 0033553104
- (b) Fox, J. M.; Katz, T. J.; Van Elshocht, S.; Verbiest, T.; Kauranen, M.; Persoons, A.; Thongpanchang, T.; Krauss, T.; Brus, L. J. Am. Chem. Soc. 1999, 121, 3453.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 3453
- Fox, J.M.¹ Katz, T.J.² Van Elshocht, S.³ Verbiest, T.⁴ Kauranen, M.⁵ Persoons, A.⁶ Thongpanchang, T.⁷ Krauss, T.⁸ Brus, L.⁹

22
- 58149329267
- Synthesis of 12 from 11 To a suspension of 11 (500 mg, 0.25 mmol) and zinc powder (1.61 g, 25.0 mmol) in dry CH2Cl2 (50 mL) was added Ac2O (2.5 mL, 24.3 mmol) and Et3N (5.0 mmol, 37.5 mmol, The mixture was stirred for 2.5 h under nitrogen at r.t, and then filtered through Celite. The filtrate was washed with 10 wt% aq HCl (50 mL) and sat. aq NaHCO3 (50 mL, The organic layer was dried over MgSO4 and evaporated in vacuo; the residue was recrystallized with hexane-CH2Cl2 to afford 12 (203 mg, 50, as green needles. Dihydropyrene 12: mp (from n-hexane-CH2Cl 2, 257-258 °C. FT-IR: 1003, 1215, 1479, 1661, 2957, 3672 cm -1. 1H NMR (400 MHz, 25°C, CDCl3, δ, 3.28 (s, 6 H, 1.61 (s, 18H, 2.58 (s, 12 H, 8.45 (s, 4 H, 13C NMR 100 MHz, 25 °C, CDCl3, δ, 20.56, 29.90
- 8: C, 70.81; H, 6.99. Found: C, 70.55; H, 7.14.

23
- 0037288094
- Chevykalova, M. N.; Manzhukova, L. F.; Artemova, N. V.; Luzikov, Yu. N.; Nifant, I. E.; Nifant, E. E. Russ. Chem. Bull. 2003, 52, 78.
- (2003) Russ. Chem. Bull , vol.52 , pp. 78
- Chevykalova, M.N.¹ Manzhukova, L.F.² Artemova, N.V.³ Luzikov, Y.N.⁴ Nifant, I.E.⁵ Nifant, E.E.⁶

24
- 58149329266
- Single crystals of 12 suitable for X-ray analysis were prepared by recrystallization from CHCl3. Diffraction data were collected on a Regaku AFCR diffractometer at 25°C with graphite monochromated Moκa (λ, 0.71069 Å) radiation. For structure analysis and refinement, computations were performed using the Crystal Structure crystallographic software package of Rigaku Corporation. The structure was solved by the direct method (SIR92, All nonhydrogen atoms were refined anisotropically. Hydrogen atoms were included, but not refined. The weighting scheme ω, 1/[σ2 (Fo2, 0.2000P)2, 0.0000P] where P, Fo2, Fc2)2. Supplementary data of 12 have been deposited with the CCDC in the CIF format (deposit No. CCDC671306, X-ray analysis for 12: C 36H42O8Cl6 C34H 40O8, 2CHCl
- a (λ = 0.71069 Å), 254 parameters, R1 = 0.1193, wR2 = 0.4244, GOF = 0.901.

25
- 0037073172
- Williams, R. V.; Armantrout, J. R.; Twamley, B.; Mitchell, R. H.; Ward, T. R.; Bandyopadhyay, S. J. Am. Chem. Soc. 2002, 124, 13495.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 13495
- Williams, R.V.¹ Armantrout, J.R.² Twamley, B.³ Mitchell, R.H.⁴ Ward, T.R.⁵ Bandyopadhyay, S.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.