SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 6, 2008, Pages 871-874

1,3-Sulfanyl group migration: Formation of unexpected trifluoromethyl- containing bridged heterocycles

(2) Jiang, Huiling a Zhu, Shizheng a

a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

4 ethoxy 1,1,1 trifluorobut 3 en 2 one; Dehydration; Indium trichloride; Michael addition; Thio nucleophiles

Indexed keywords

1,1,1 TRIFLUORO 4,4 BIS(ARYLTHIO)BUTANE 2,2 DIOL; BUTANE; FLUORINE DERIVATIVE; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; SULFURIC ACID; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; HYDRATION; X RAY DIFFRACTION;

EID: 42149165527 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042909 Document Type: Article

Times cited : (2)

References (23)

1
- 23144460714
- Morehead, A.; Grubbs, R. Chem. Commun. 1998, 275.
- (1998) Chem. Commun , pp. 275
- Morehead, A.¹ Grubbs, R.²

2
- 0003075009
- (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 1.
- (1997) Top. Curr. Chem , vol.190 , pp. 1
- Chiu, P.¹ Lautens, M.²

3
- 0032585375
- (b) Bernardelli, P.; Paquette, L. A. Heterocycles 1998, 49, 531.
- (1998) Heterocycles , vol.49 , pp. 531
- Bernardelli, P.¹ Paquette, L.A.²

4
- 0033607764
- (c) Vogel, P.; Cossy, J.; Plumet, J.; Arjona, O. Tetrahedron 1999, 55, 13521.
- (1999) Tetrahedron , vol.55 , pp. 13521
- Vogel, P.¹ Cossy, J.² Plumet, J.³ Arjona, O.⁴

5
- 0030048612
- Isolation: Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanihi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara, M. J. Antibiot. 1996, 49, 37.
- (a) Isolation: Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanihi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara, M. J. Antibiot. 1996, 49, 37.

6
- 0033199676
- Total synthesis: Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778
- (b) Total synthesis: Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778

7
- 0030944697
- (c) Matzanke, N.; Gregg, R. J.; Weinreb, S. M. J. Org. Chem. 1997, 62, 1920.
- (1997) J. Org. Chem , vol.62 , pp. 1920
- Matzanke, N.¹ Gregg, R.J.² Weinreb, S.M.³

8
- 0033522861
- (a) Banihashemi, A.; Rahmatpour, A. Tetrahedron 1999, 55, 7271.
- (1999) Tetrahedron , vol.55 , pp. 7271
- Banihashemi, A.¹ Rahmatpour, A.²

9
- 0034700824
- (b) Kazunari, K.; Masaaki, K.; Kiyoshi, F.; Takashi, T.; Takashi, S.; Naoki, M.; Masatake, T. Tetrahedron Lett. 2000, 41, 485.
- (2000) Tetrahedron Lett , vol.41 , pp. 485
- Kazunari, K.¹ Masaaki, K.² Kiyoshi, F.³ Takashi, T.⁴ Takashi, S.⁵ Naoki, M.⁶ Masatake, T.⁷

10
- 0000212607
- Sole, D.; Peidro, E.; Bonjoch, J. Org. Lett. 2000, 2, 2225.
- (2000) Org. Lett , vol.2 , pp. 2225
- Sole, D.¹ Peidro, E.² Bonjoch, J.³

11
- 8844222050
- Mashraqui, S. H.; Patil, M. B.; Mistry, H. D.; Ghadigaonkar, S.; Meetsma, A. Chem. Lett. 2004, 33, 1058.
- (2004) Chem. Lett , vol.33 , pp. 1058
- Mashraqui, S.H.¹ Patil, M.B.² Mistry, H.D.³ Ghadigaonkar, S.⁴ Meetsma, A.⁵

12
- 2942589152
- Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
- (2004) Chem. Rev , vol.104 , pp. 2199
- Deiters, A.¹ Martin, S.F.²

13
- 43949166113
- Gorbunova, M. G.; Gerus, I. I.; Kukhar, V. P. J. Fluorine Chem. 1993, 65, 25.
- (1993) J. Fluorine Chem , vol.65 , pp. 25
- Gorbunova, M.G.¹ Gerus, I.I.² Kukhar, V.P.³

14
- 33744473053
- Zhu, S. Z.; Jin, G. F.; Jiang, H. L. Can. J. Chem. 2005, 83, 2127.
- (2005) Can. J. Chem , vol.83 , pp. 2127
- Zhu, S.Z.¹ Jin, G.F.² Jiang, H.L.³

15
- 0031138623
- Vdovenko, S. I.; Gerus, I. L; Gorbunova, M. G. J. Fluorine Chem. 1997, 82, 167.
- (1997) Fluorine Chem , vol.82 , pp. 167
- Vdovenko, S.I.¹ Gerus, I.L.² Gorbunova, M.G.J.³

16
- 0024445182
- (a) Masaru, H.; Ryoichi, M.; Etsuji, O.; Syuhei, S.; Hitoshi, N.; Katsushi, M. Tetrahedron Lett. 1989, 30, 6173.
- (1989) Tetrahedron Lett , vol.30 , pp. 6173
- Masaru, H.¹ Ryoichi, M.² Etsuji, O.³ Syuhei, S.⁴ Hitoshi, N.⁵ Katsushi, M.⁶

17
- 2142836711
- (b) Gerus, I. L; Gorbunova, M. G.; Vdovenko, S. I.; Yagupol'skii, Y. u. L.; Kukhar', V. P. J. Org. Chem. USSR (Engl. Transl.) 1990, 26, 1623.
- (1990) J. Org. Chem. USSR (Engl. Transl.) , vol.26 , pp. 1623
- Gerus, I.L.¹ Gorbunova, M.G.² Vdovenko, S.I.³ Yagupol'skii, Y.U.L.⁴ Kukhar', V.P.⁵

18
- 20744454937
- Zhu, S. Z.; Jiang, H. L.; Jin, G. F. J. Fluorine Chem. 2005, 126, 931.
- (2005) Fluorine Chem , vol.126 , pp. 931
- Zhu, S.Z.¹ Jiang, H.L.² Jin, G.F.J.³

19
- 20544436125
- Garg, S. K.; Kumar, R.; Chakraborti, A. K. Synlett 2005, 1370.
- (2005) Synlett , pp. 1370
- Garg, S.K.¹ Kumar, R.² Chakraborti, A.K.³

20
- 42149098487
- Typical Procedure and Spectroscopic Data of Compounds 2 and 3 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one(1, 0.336 g, 2 mmol) was added into a 10 mL flask containing thiol (4 mmol, which was stirred at r.t, TLC analysis was used to monitor the reaction progress. After 2-4 d, the reaction was deemed complete, and the reaction mixture was purified by column chromatography on silica gel (hexane-EtOAc, 200:3) to give the products 2 or 3. 1,1,1,-Tritluoro-4,4-bis(phenylthio)butane-2,2-diol (2a) Yellow solid, mp 62-63°C; yield 72, 1NMR (300 MHz, CDCl3, δ, 7.54-7.28 (10 H, m, 2 C6H5, 4.92 (1 H, t, 3JHH, 7.0 Hz, CH, 4.68 (2 H, br, OH, 2.37 (2 H, d, 3JHH, 7.0 Hz, CH2, 13C NMR (75 MHz, CDCl3, δ, 42.63 (CH2, 51.97 (CH, 115.17 q, 1JCF, 233.3 Hz, CF3, 129.91
- 3SCl (%): C, 43.58; H, 4.27. Found: C, 43.56; H, 4.26.

21
- 42149129257
- Typical Procedure and Spectroscopic Data for Diols 4,4-Diethoxy-1,1,1-trifluorobutane-2,2-diol (5, 0.1 g, 0.5 mmol) was added into a 10 mL flask containing thiol (2 mmol, which was stirred at r.t, TLC analysis was used to monitor the process. After 3 d, the reaction finished, and the reaction mixture was purified by column chromatography on silica gel (hexane-EtOAc, 100:1) to give the products 2d or 2e. 4,4-Bis(4-chlorophenylthio)-1,1,1-trifluorobutane-2,2-diol (2d) Yellow solid, mp 66-67°C; yield 73, 1NMR (300 MHz, CDCl3, δ, 7.41 (4 H, d, 3JHH, 6.0 Hz, C 6H4, 7.34 (4 H, d, 3JHH, 6.0 Hz, C6H4, 4.83 (1 H, t, 3J HH, 6.0 Hz, CH, 4.53 (2 H, s, OH, 2.31 (2 H, d, 3JHH, 8.0 Hz, CH2, 19F NMR (298 MHz, CDCl3, δ, 86.99 s, C
- 2 (%): C, 44.77; H, 3.05. Found: C, 44.83; H, 3.01.

22
- 42149105449
- Typical Procedure and Spectroscopic Data for Bridged Cyclic Compounds Compound 2 was added to the cold coned H2SO 4 (3 mL) with efficient stirring. The temperature of the reaction during the addition was kept below 10°C and the reaction mixture was stirred at 0°C for 1 h. Then it was poured to the chipped ice and set aside for 2 h in the refrigerator. The aqueous acid solution was extracted with CH 2Cl2 (3 x 10 mL, The solvent was evaporated in vacuum to give the crude products, which were purified by recrystallization (CH 2Cl2-hexane) to give the final product 4 and/or 6. Compound 4a: white solid, mp 169-171°C; yield >99, 1H NMR (300 MHz, CDCl3, δ, 7.45-7.14 (8 H, m, 2 C6H4, 4.48 (1 H, s, CH, 2.61 (2 H, d, 3JHH, 4.0 Hz, CH2, 19F NMR 298 MHz, CDCl3
- 3OS (%): C, 45.04; H, 2.27. Found: C, 44.84; H, 2.24.

23
- 42149092415
- Single-crystal X-ray structural data for 4a have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 644817.
- Single-crystal X-ray structural data for 4a have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 644817.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.