SCOPUS 정보 검색 플랫폼

European Journal of Organic Chemistry

Volumn , Issue 19, 2003, Pages 3827-3831

Bismuth triflate: An efficient catalyst for the formation and deprotection of tetrahydropyranyl ethers

(6) Stephens, Jacqueline R a Butler, Phillip L a Clow, Curtis H a Oswald, Matthew C a Smith, Russell C a Mohan, Ram S a

a ILLINOIS WESLEYAN UNIVERSITY (United States)

Author keywords

Bismuth; Bismuth triflate; Environment friendly catalysts; Lewis acids; Tetrahydropyranyl ethers

Indexed keywords

ALCOHOL DERIVATIVE; BISMUTH DERIVATIVE; BISMUTH TRIFLATE; DICHLOROMETHANE; LEWIS ACID; PHENOL DERIVATIVE; TETRAHYDROPYRANYL ETHER; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; DEPROTECTION REACTION; GAS CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MOISTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0141995088 PISSN: 1434193X EISSN: None Source Type: Journal
DOI: 10.1002/ejoc.200300295 Document Type: Article

Times cited : (64)

References (58)

1
- 33947443299
- [1a] W. E. Parham, E. L. Anderson, J. Am. Chem. Soc. 1948, 70, 4187-4189.
- (1948) J. Am. Chem. Soc. , vol.70 , pp. 4187-4189
- Parham, W.E.¹ Anderson, E.L.²

2
- 0003463148
- John Wiley & Sons, Inc., New York
- [1b] T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., John Wiley & Sons, Inc., New York, 1999.
- (1999) Protective Groups in Organic Synthesis, 3rd Ed.
- Greene, T.W.¹ Wuts, P.G.M.²

3
- 0003463150
- Blackwell Science, Inc., Malden, MA
- [1c] J. R. Hanson, Protecting Groups in Organic Synthesis, 1st ed., Blackwell Science, Inc., Malden, MA, 1999.
- (1999) Protecting Groups in Organic Synthesis, 1st Ed.
- Hanson, J.R.¹

4
- 0003405157
- Georg Thieme Verlag, Stuttgart
- [1d] Kocienski, P. J. Protecting Groups, 1st ed., Georg Thieme Verlag, Stuttgart, 1994.
- (1994) Protecting Groups, 1st Ed.
- Kocienski, P.J.¹

5
- 84986685047
- J. H. van Boom, J. D. M. Herschied, C. B. Reese, Synthesis 1973, 169-170.
- (1973) Synthesis , pp. 169-170
- Van Boom, J.H.¹ Herschied, J.D.M.² Reese, C.B.³

6
- 33744586503
- M. Miyashita, A. Yoshikoshi, P. A. Grieco, J. Org. Chem. 1977, 42, 3772-3774.
- (1977) J. Org. Chem. , vol.42 , pp. 3772-3774
- Miyashita, M.¹ Yoshikoshi, A.² Grieco, P.A.³

7
- 85068721128
- A. Bongini, G. Cardillo, M. Orena, S. Sandri, Synthesis 1979, 618-620.
- (1979) Synthesis , pp. 618-620
- Bongini, A.¹ Cardillo, G.² Orena, M.³ Sandri, S.⁴

8
- 2042432431
- Y. Morizawa, I. Mori, T. Hiyama, H. Nozaki, Synthesis 1981, 899-901.
- (1981) Synthesis , pp. 899-901
- Morizawa, Y.¹ Mori, I.² Hiyama, T.³ Nozaki, H.⁴

9
- 84986511440
- G. A. Olah, A. Husain, B. P. Singh, Synthesis 1983, 892-895.
- (1983) Synthesis , pp. 892-895
- Olah, G.A.¹ Husain, A.² Singh, B.P.³

10
- 84986728802
- G. A. Olah, A. Husain, B. P. Singh, Synthesis 1985, 703-704.
- (1985) Synthesis , pp. 703-704
- Olah, G.A.¹ Husain, A.² Singh, B.P.³

11
- 84988053093
- S. Hoyer, P. Laszlo, M. Orlovic, E. Polla, Synthesis 1986, 655-657.
- (1986) Synthesis , pp. 655-657
- Hoyer, S.¹ Laszlo, P.² Orlovic, M.³ Polla, E.⁴

12
- 84986961497
- R. D. Johnston, C. R. Marston, P. E. Krieger, G. L. Goe, Synthesis 1988, 393-394.
- (1988) Synthesis , pp. 393-394
- Johnston, R.D.¹ Marston, C.R.² Krieger, P.E.³ Goe, G.L.⁴

13
- 0001744693
- V. Bolitt, C. Mioskowski, D.-S. Shin, J. R. Falck, Tetrahedron Lett. 1988, 29, 4583-4586.
- (1988) Tetrahedron Lett. , vol.29 , pp. 4583-4586
- Bolitt, V.¹ Mioskowski, C.² Shin, D.-S.³ Falck, J.R.⁴

14
- 0027195506
- G. Maity, S. C. Roy, Synth. Commun. 1993, 23, 1667-1671.
- (1993) Synth. Commun. , vol.23 , pp. 1667-1671
- Maity, G.¹ Roy, S.C.²

15
- 0027362616
- P. Kumar, C. U. Dinesh, R. S. Reddy, B. Pandey, Synthesis 1993, 1069-1070.
- (1993) Synthesis , pp. 1069-1070
- Kumar, P.¹ Dinesh, C.U.² Reddy, R.S.³ Pandey, B.⁴

16
- 0028277705
- J. M. Campelo, A. Garcia, F. Lafont, D. Luna, J. M. Marinas, Synth. Commun. 1994, 24, 1345-1350.
- (1994) Synth. Commun. , vol.24 , pp. 1345-1350
- Campelo, J.M.¹ Garcia, A.² Lafont, F.³ Luna, D.⁴ Marinas, J.M.⁵

17
- 33751158647
- B. C. Ranu, M. Saha, J. Org. Chem. 1994, 59, 8269-8270.
- (1994) J. Org. Chem. , vol.59 , pp. 8269-8270
- Ranu, B.C.¹ Saha, M.²

18
- 0141991443
- Á. Molnár, T Beregszászi, Tetrahedron Lett. 1996, 37, 8597-8600.
- (1996) Tetrahedron Lett. , vol.37 , pp. 8597-8600
- Molnár, Á.¹ Beregszászi, T.²

19
- 0030017024
- U. T. Bhalerao, K. J. Davis, B. V. Rao, Synth. Commun. 1996, 26, 3081-3085.
- (1996) Synth. Commun. , vol.26 , pp. 3081-3085
- Bhalerao, U.T.¹ Davis, K.J.² Rao, B.V.³

20
- 0032506627
- B. S. Babu, K. K. Balasubramanian, Tetrahedron Lett. 1998, 39, 9287-9288.
- (1998) Tetrahedron Lett. , vol.39 , pp. 9287-9288
- Babu, B.S.¹ Balasubramanian, K.K.²

21
- 0033788896
- A. M. Reddy, R. L. Reddy, N. Bhanumathi, R. K. Rao, Synth. Commun. 2000, 30, 4323-4328.
- (2000) Synth. Commun. , vol.30 , pp. 4323-4328
- Reddy, A.M.¹ Reddy, R.L.² Bhanumathi, N.³ Rao, R.K.⁴

22
- 0035540607
- J.-E. Choi, K.-Y. Ko, Bull. Korean Chem. Soc. 2001, 22, 1177-1178.
- (2001) Bull. Korean Chem. Soc. , vol.22 , pp. 1177-1178
- Choi, J.-E.¹ Ko, K.-Y.²

23
- 0035832076
- M. H. Habibi, S. Tangestaninejad, I. Mohammadpoor-Baltork, V. Mirkhani, B. Yadollahi, Tetrahedron Lett. 2001, 42, 2851-2853.
- (2001) Tetrahedron Lett. , vol.42 , pp. 2851-2853
- Habibi, M.H.¹ Tangestaninejad, S.² Mohammadpoor-Baltork, I.³ Mirkhani, V.⁴ Yadollahi, B.⁵

24
- 0003573092
- Reinhold Van Nostrand, New York
- [21a] N. Irwing-Sax, R. J. Bewis, Dangerous Properties of Industrial Materials, Reinhold Van Nostrand, New York, 1989, p. 283-284.
- (1989) Dangerous Properties of Industrial Materials , pp. 283-284
- Irwing-Sax, N.¹ Bewis, R.J.²

25
- 0003573092
- Reinhold Van Nostrand, New York
- [21b] N. Irwing-Sax, R. J. Bewis, Dangerous Properties of Industrial Materials, Reinhold Van Nostrand, New York, 1989, p. 522-523.
- (1989) Dangerous Properties of Industrial Materials , pp. 522-523
- Irwing-Sax, N.¹ Bewis, R.J.²

26
- 0003565144
- (Ed. S. Patai), Wiley, New York
- [21c] U. Wormser, I. Nir, in The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds (Ed. S. Patai), Wiley, New York, 1994, p. 715-723.
- (1994) The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds , pp. 715-723
- Wormser, U.¹ Nir, I.²

27
- 0003565144
- (Ed. S. Patai), Wiley, New York
- [21d] K. Dill, E. L. McGowan, in The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds (Ed. S. Patai), Wiley, New York, 1994, p. 695-713.
- (1994) The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds , pp. 695-713
- Dill, K.¹ McGowan, E.L.²

28
- 0003565144
- (Ed. S. Patai), Wiley, New York
- [21e] S. Maeda, in The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds (Ed. S. Patai), Wiley, New York, 1994, p. 725-759.
- (1994) The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds , pp. 725-759
- Maeda, S.¹

29
- 0004211783
- London, chapter 8
- [22a] J. Reglinski, in Chemistry of Arsenic, Antimony and Bismuth, Blackie Academic and Professional, London, 1998, chapter 8, pp. 403-440.
- (1998) Chemistry of Arsenic, Antimony and Bismuth, Blackie Academic and Professional , pp. 403-440
- Reglinski, J.¹

30
- 0141922273
- note
- 3 (10.2 mg/kg).

31
- 0030830364
- [23a] J. R. Desmurs, M. Labrouillère, C. Le Roux, H. Gaspard, A. Laporterie, J. Dubac, Tetrahedron Lett. 1997, 38, 8871-8874.
- (1997) Tetrahedron Lett. , vol.38 , pp. 8871-8874
- Desmurs, J.R.¹ Labrouillère, M.² Le Roux, C.³ Gaspard, H.⁴ Laporterie, A.⁵ Dubac, J.⁶

32
- 2742553341
- [23b] S. Répichet, C. Le Roux, J. Dubac, J. R. Desmurs, Eur. J. Org. Chem. 1998, 2743-2746.
- (1998) Eur. J. Org. Chem. , pp. 2743-2746
- Répichet, S.¹ Le Roux, C.² Dubac, J.³ Desmurs, J.R.⁴

33
- 0141601826
- S. Répichet, C. Le Roux, P. Hernandez, J. Dubac, J. Org. Chem. 1999, 64, 6479-6482.
- (1999) J. Org. Chem. , vol.64 , pp. 6479-6482
- Répichet, S.¹ Le Roux, C.² Hernandez, P.³ Dubac, J.⁴

34
- 0001681930
- [25a] B. Garrigues, F. Gonzaga, H. Robert, J. Dubac, J. Org. Chem. 1997, 62, 4880-4882.
- (1997) J. Org. Chem. , vol.62 , pp. 4880-4882
- Garrigues, B.¹ Gonzaga, F.² Robert, H.³ Dubac, J.⁴

35
- 0032485232
- [25b] H. Robert, B. Garrigues, J. Dubac, Tetrahedron Lett. 1998, 39, 1161-1164.
- (1998) Tetrahedron Lett. , vol.39 , pp. 1161-1164
- Robert, H.¹ Garrigues, B.² Dubac, J.³

36
- 0033902629
- H. Laurent-Robert, B. Garrigues, J. Dubac, Synlett 2000, 1160-1162.
- (2000) Synlett , pp. 1160-1162
- Laurent-Robert, H.¹ Garrigues, B.² Dubac, J.³

37
- 0035851385
- K. A. Bhatia, K. J. Eash, N. M. Leonard, M. C. Oswald, R. S. Mohan, Tetrahedron Lett. 2001, 42, 8129-8132.
- (2001) Tetrahedron Lett. , vol.42 , pp. 8129-8132
- Bhatia, K.A.¹ Eash, K.J.² Leonard, N.M.³ Oswald, M.C.⁴ Mohan, R.S.⁵

38
- 0035851387
- M. D. Carrigan, K. J. Eash, M. C. Oswald, R. S. Mohan, Tetrahedron Lett. 2001, 42, 8133-8135.
- (2001) Tetrahedron Lett. , vol.42 , pp. 8133-8135
- Carrigan, M.D.¹ Eash, K.J.² Oswald, M.C.³ Mohan, R.S.⁴

39
- 0037039957
- [29a] M. C. Carrigan, D. Sarapa, R. C. Smith, L. C. Wieland, R. S. Mohan, J. Org. Chem. 2002, 67, 1027-1030.
- (2002) J. Org. Chem. , vol.67 , pp. 1027-1030
- Carrigan, M.C.¹ Sarapa, D.² Smith, R.C.³ Wieland, L.C.⁴ Mohan, R.S.⁵

40
- 0037178495
- [29b] N. M. Leonard, M. C. Oswald, D. A. Freiberg, B. A. Nattier, R. C. Smith, R. S. Mohan, J. Org. Chem. 2002, 67, 5202-5207.
- (2002) J. Org. Chem. , vol.67 , pp. 5202-5207
- Leonard, N.M.¹ Oswald, M.C.² Freiberg, D.A.³ Nattier, B.A.⁴ Smith, R.C.⁵ Mohan, R.S.⁶

41
- 0033534338
- M. Labrouillère, C. Le Roux, H. Gaspard, A. Laporterie, J. Dubac, J. R. Desmurs, Tetrahedron Lett. 1999, 40, 285-286. Bismuth triflate synthesized by this procedure is reported to be mainly the tetrahydrate. Recently, another procedure for the synthesis of bismuth triflate has been reported: S. Répichet, A. Zwick, L. Vendier, C. Le Roux, J. Dubac, Tetrahedron Lett. 2002, 43, 993-995.
- (1999) Tetrahedron Lett. , vol.40 , pp. 285-286
- Labrouillère, M.¹ Le Roux, C.² Gaspard, H.³ Laporterie, A.⁴ Dubac, J.⁵ Desmurs, J.R.⁶

42
- 0037016958
- M. Labrouillère, C. Le Roux, H. Gaspard, A. Laporterie, J. Dubac, J. R. Desmurs, Tetrahedron Lett. 1999, 40, 285-286. Bismuth triflate synthesized by this procedure is reported to be mainly the tetrahydrate. Recently, another procedure for the synthesis of bismuth triflate has been reported: S. Répichet, A. Zwick, L. Vendier, C. Le Roux, J. Dubac, Tetrahedron Lett. 2002, 43, 993-995.
- (2002) Tetrahedron Lett. , vol.43 , pp. 993-995
- Répichet, S.¹ Zwick, A.² Vendier, L.³ Le Roux, C.⁴ Dubac, J.⁵

43
- 0141991442
- 13C NMR (15 peaks): δ = 23.4, 25.8, 31.4, 69.7, 78.9, 116.6, 119.7, 120.8, 122.6, 126.4, 128.6, 128.8, 129.3, 130.7, 153.6 ppm.
- (1988) Aust. J. Chem. , vol.42 , pp. 69-80
- Pinhey, J.T.¹ Xuan, P.T.²

44
- 0029060380
- S. Raina, V. K. Singh, Synth. Commun. 1995, 25, 2395-2400.
- (1995) Synth. Commun. , vol.25 , pp. 2395-2400
- Raina, S.¹ Singh, V.K.²

45
- 0000416631
- G. Maiti, S. C. Roy, J. Org. Chem. 1996, 61, 6038-6039.
- (1996) J. Org. Chem. , vol.61 , pp. 6038-6039
- Maiti, G.¹ Roy, S.C.²

46
- 0033547965
- A. S.-Y. Lee, F.-Y. Su, Y.-C. Liao, Tetrahedron Lett. 1999, 40, 1323-1326.
- (1999) Tetrahedron Lett. , vol.40 , pp. 1323-1326
- Lee, A.S.-Y.¹ Su, F.-Y.² Liao, Y.-C.³

47
- 0033166815
- I. E. Markó, A. Ates, B. Augustyns, A. Gautier, Y. Quesnel, L. Turet, M. Wiaux, Tetrahedron Lett. 1999, 40, 5613-5616.
- (1999) Tetrahedron Lett. , vol.40 , pp. 5613-5616
- Markó, I.E.¹ Ates, A.² Augustyns, B.³ Gautier, A.⁴ Quesnel, Y.⁵ Turet, L.⁶ Wiaux, M.⁷

48
- 0034033756
- K. J. Davis, U. T. Bhalrao, B. V. Rao, Synth. Commun. 2000, 30, 2301-2308.
- (2000) Synth. Commun. , vol.30 , pp. 2301-2308
- Davis, K.J.¹ Bhalrao, U.T.² Rao, B.V.³

49
- 0034897215
- T. Oriyama, T. Watahiki, Y. Kogayashi, H. Hirano, T. Suzuki, Synth. Commun. 2001, 31, 2305-2311.
- (2001) Synth. Commun. , vol.31 , pp. 2305-2311
- Oriyama, T.¹ Watahiki, T.² Kogayashi, Y.³ Hirano, H.⁴ Suzuki, T.⁵

50
- 0027169684
- K. Nishitani, Y. Nakamura, R. Orii, C. Arai, K. Yamakawa, Chem. Pharm. Bull. 1993, 41, 822-831.
- (1993) Chem. Pharm. Bull. , vol.41 , pp. 822-831
- Nishitani, K.¹ Nakamura, Y.² Orii, R.³ Arai, C.⁴ Yamakawa, K.⁵

51
- 0001280103
- K. H. Cha, T. W. Kang, H.-W. Lee, E.-N. Kim, N.-H. Choi, J.-W. Kim, C. Hong, Synth. Commun. 1998, 28, 2131-2136.
- (1998) Synth. Commun. , vol.28 , pp. 2131-2136
- Cha, K.H.¹ Kang, T.W.² Lee, H.-W.³ Kim, E.-N.⁴ Choi, N.-H.⁵ Kim, J.-W.⁶ Hong, C.⁷

52
- 0033593492
- I. Berque, P. Ménez, P. Razon, J. Mahuteau, J.-P Férézou, A. Pancrazi, J. Ardisson, J.-D. Brion, J. Org. Chem. 1999, 64, 373-381.
- (1999) J. Org. Chem. , vol.64 , pp. 373-381
- Berque, I.¹ Ménez, P.² Razon, P.³ Mahuteau, J.⁴ Férézou, J.-P.⁵ Pancrazi, A.⁶ Ardisson, J.⁷ Brion, J.-D.⁸

53
- 0141922272
- R. R. Fraser, P. Hanbury, C. Reyes-Zamora, Can. J. Chem. 1967, 45, 2481-2491.
- (1967) Can. J. Chem. , vol.45 , pp. 2481-2491
- Fraser, R.R.¹ Hanbury, P.² Reyes-Zamora, C.³

54
- 0141991441
- D. N. Robertson, J. Org. Chem. 1960, 25, 931-932.
- (1960) J. Org. Chem. , vol.25 , pp. 931-932
- Robertson, D.N.¹

55
- 0141887758
- [43a] F. Lafuma, C. Quivoron, G. Champetier, C. R. Acad. Sci. Paris, Ser C 1971, 272, 2020-2022.
- (1971) C. R. Acad. Sci. Paris, Ser. C , vol.272 , pp. 2020-2022
- Lafuma, F.¹ Quivoron, C.² Champetier, G.³

56
- 84989052088
- [43b] A. J. de Hoog, Org. Magn. Reson. 1974, 6, 233-235.
- (1974) Org. Magn. Reson. , vol.6 , pp. 233-235
- De Hoog, A.J.¹

57
- 0035833043
- [43c] Y.-S. Hon, C.-F. Lee, R.-J. Chen, P.-H. Szu, Tetrahedron 2001, 57, 5991-6001.
- (2001) Tetrahedron , vol.57 , pp. 5991-6001
- Hon, Y.-S.¹ Lee, C.-F.² Chen, R.-J.³ Szu, P.-H.⁴

58
- 0036287692
- I. Mohammadpor-Baltork, B. Kharamesh, S. Kolagar, Synth. Commun. 2002, 32, 1633-1637.
- (2002) Synth. Commun. , vol.32 , pp. 1633-1637
- Mohammadpor-Baltork, I.¹ Kharamesh, B.² Kolagar, S.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.