SCOPUS 정보 검색 플랫폼

Volumn , Issue 11, 2009, Pages 1803-1805

Nucleophilic ring opening of mono-activated cyclopropanes with arylselenolates generated from diselenides in the presence of a Zn/AlCl 3 system

(2) Nazari, Mohammad a Movassagh, Barahman a

a K N TOOSI UNIVERSITY OF TECHNOLOGY (Iran)

Author keywords

Diselenides; Mono activated cyclopropanes; Ring opening; Zinc; Zinc selenolates

Indexed keywords

ALDEHYDE; ALUMINUM CHLORIDE; CYCLOPROPANE DERIVATIVE; DISELENIDE; GAMMA ARYLSELENENYL KETONE; KETONE; KETONE DERIVATIVE; NITRILE; NUCLEOPHILE; ORGANOSELENIUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SELENIDE; UNCLASSIFIED DRUG; ZINC; ZINC SELENOLATE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; THIN LAYER CHROMATOGRAPHY;

EID: 67650032597 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217372 Document Type: Article

Times cited : (6)

References (35)

1
- 0004112606
- Wiley: New York
- (a) Liotta, D. Organoselenium Chemistry; Wiley: New York, 1987.
- (1987) Organoselenium Chemistry
- Liotta, D.¹

2
- 0003441989
- Oxford University Press: Oxford U. K
- (b) Back, T. G. Organoselenium Chemistry: A Practical Approach; Oxford University Press: Oxford U. K., 1999.
- (1999) Organoselenium Chemistry: A Practical Approach
- Back, T.G.¹

3
- 0035385139
- (a) Mugesh, G.; du Mont, W. W.; Sies, H. Chem. Rev. 2001, 101, 2125.
- (2001) Chem. Rev , vol.101 , pp. 2125
- Mugesh, G.¹ du Mont, W.W.² Sies, H.³

4
- 0034822872
- (b) Malmstrom, J.; Jonsson, M.; Cotgreave, I. A.; Hammarstrom, L.; Sjodin, M.; Engman, L. J. Am. Chem. Soc. 2001, 123, 3434.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 3434
- Malmstrom, J.¹ Jonsson, M.² Cotgreave, I.A.³ Hammarstrom, L.⁴ Sjodin, M.⁵ Engman, L.⁶

5
- 0242270866
- (c) Back, T. G.; Moussa, Z. J. Am. Chem. Soc. 2003, 125, 13455.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 13455
- Back, T.G.¹ Moussa, Z.²

6
- 0034625381
- (d) Lucas, M. A.; Nagugen, O. T. K.; Schiesser, C. H.; Zheng, S. L. Tetrahedron 2000, 56, 3995.
- (2000) Tetrahedron , vol.56 , pp. 3995
- Lucas, M.A.¹ Nagugen, O.T.K.² Schiesser, C.H.³ Zheng, S.L.⁴

7
- 0004112606
- Liotta, D, Ed, Wiley: New York
- Monahan, R.; Brown, D.; Waykole, L.; Liotta, D. In Organoselenium Chemistry; Liotta, D., Ed.; Wiley: New York, 1987.
- (1987) Organoselenium Chemistry
- Monahan, R.¹ Brown, D.² Waykole, L.³ Liotta, D.⁴

8
- 0007590568
- (a) Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697.
- (1973) J. Am. Chem. Soc , vol.95 , pp. 2697
- Sharpless, K.B.¹ Lauer, R.F.²

9
- 0002819592
- (b) Aynsley, E. E.; Greenwood, N. N.; Leach, J. B. Chem. Ind. (London) 1966, 379.
- (1966) Chem. Ind. (London) , pp. 379
- Aynsley, E.E.¹ Greenwood, N.N.² Leach, J.B.³

10
- 0027523028
- (c) Zhang, Y.; Yu, Y.; Lin, R. Synth. Commun. 1993, 23, 189.
- (1993) Synth. Commun , vol.23 , pp. 189
- Zhang, Y.¹ Yu, Y.² Lin, R.³

11
- 0002032453
- (d) Suzuki, H.; Yoshinaga, M.; Takaoka, K.; Hiroi, Y. Synthesis 1985, 497.
- (1985) Synthesis , pp. 497
- Suzuki, H.¹ Yoshinaga, M.² Takaoka, K.³ Hiroi, Y.⁴

12
- 0000821865
- (e) Liotta, D.; Sunay, U.; Santiesteban, H.; Markiewicz, W. J. Org. Chem. 1981, 46, 2605.
- (1981) J. Org. Chem , vol.46 , pp. 2605
- Liotta, D.¹ Sunay, U.² Santiesteban, H.³ Markiewicz, W.⁴

13
- 0010466825
- (f) Taboury, F. Bull. Soc. Chem. Fr. 1903, 29, 761.
- (1903) Bull. Soc. Chem. Fr , vol.29 , pp. 761
- Taboury, F.¹

14
- 49349140545
- (g) Liotta, D.; Markiewicz, W.; Santiesteban, H. Tetrahedron Lett. 1977, 4365.
- (1977) Tetrahedron Lett , pp. 4365
- Liotta, D.¹ Markiewicz, W.² Santiesteban, H.³

15
- 0001497231
- (h) Liotta, D.; Santiesteban, H. Tetrahedron Lett. 1977, 4369.
- (1977) Tetrahedron Lett , pp. 4369
- Liotta, D.¹ Santiesteban, H.²

16
- 0043104432
- (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66.
- (1979) Acc. Chem. Res , vol.12 , pp. 66
- Danishefsky, S.¹

17
- 0008246807
- (b) Danishefsky, S.; Mckee, R.; Singh, R. K. J. Am. Chem. Soc. 1977, 99, 4783.
- (1977) J. Am. Chem. Soc , vol.99 , pp. 4783
- Danishefsky, S.¹ Mckee, R.² Singh, R.K.³

18
- 0000086277
- (a) Wrobel, T.; Takahashi, K.; Honkan, V.; Lannoye, G.; Cook, T. M.; Bertz, S. H. J. Org. Chem. 1983, 48, 139.
- (1983) J. Org. Chem , vol.48 , pp. 139
- Wrobel, T.¹ Takahashi, K.² Honkan, V.³ Lannoye, G.⁴ Cook, T.M.⁵ Bertz, S.H.⁶

19
- 0005667137
- (b) Zutterman, E.; De Wilde, H.; Mijngheer, R.; De Clercq, P.; Vandewalle, H. Tetrahedron 1979, 35, 2389.
- (1979) Tetrahedron , vol.35 , pp. 2389
- Zutterman, E.¹ De Wilde, H.² Mijngheer, R.³ De Clercq, P.⁴ Vandewalle, H.⁵

20
- 0017772413
- (a) Taber, D. F. J. Am. Chem. Soc. 1977, 99, 3513.
- (1977) J. Am. Chem. Soc , vol.99 , pp. 3513
- Taber, D.F.¹

21
- 0007402952
- (b) Caputo, R.; Ferreri, C.; Palumbo, G. Tetrahedron Lett. 1984, 25, 577.
- (1984) Tetrahedron Lett , vol.25 , pp. 577
- Caputo, R.¹ Ferreri, C.² Palumbo, G.³

22
- 0002167515
- (c) Kondo, K.; Umemoto, T.; Takahatake, Y.; Tunemoto, D. Tetrahedron Lett. 1977, 23, 113.
- (1977) Tetrahedron Lett , vol.23 , pp. 113
- Kondo, K.¹ Umemoto, T.² Takahatake, Y.³ Tunemoto, D.⁴

23
- 0001507667
- Meinwald, J.; Crandall, K. J. Am. Chem. Soc. 1966, 88, 1292.
- (1966) J. Am. Chem. Soc , vol.88 , pp. 1292
- Meinwald, J.¹ Crandall, K.²

24
- 0037891233
- Smith, A. B.; Scarborough, R. M. Jr. Tetrahedron Lett. 1978, 1649.
- (1978) Tetrahedron Lett , pp. 1649
- Smith, A.B.¹ Scarborough Jr., R.M.²

25
- 0001497214
- Scarborough, R. M. Jr.; Toder, B. H.; Smith, A. B. III. J. Am. Chem. Soc. 1980, 102, 3904.
- (1980) J. Am. Chem. Soc , vol.102 , pp. 3904
- Scarborough Jr., R.M.¹ Toder, B.H.² Smith III, A.B.³

26
- 59649095676
- (a) Nazari, M.; Movassagh, B. Tetrahedron Lett. 2009, 50, 1453.
- (2009) Tetrahedron Lett , vol.50 , pp. 1453
- Nazari, M.¹ Movassagh, B.²

27
- 57149141365
- (b) Nazari, M.; Movassagh, B. Tetrahedron Lett. 2009, 50, 438.
- (2009) Tetrahedron Lett , vol.50 , pp. 438
- Nazari, M.¹ Movassagh, B.²

28
- 34547617208
- (c) Movassagh, B.; Tatar, A. Synlett 2007, 1954.
- (2007) Synlett , pp. 1954
- Movassagh, B.¹ Tatar, A.²

29
- 0037757934
- (d) Movassagh, B.; Mirshojaei, F. Monatsh. Chem. 2003, 134, 831.
- (2003) Monatsh. Chem , vol.134 , pp. 831
- Movassagh, B.¹ Mirshojaei, F.²

30
- 19944373067
- (e) Movassagh, B.; Shamsipoor, M. Synlett 2005, 1316.
- (2005) Synlett , pp. 1316
- Movassagh, B.¹ Shamsipoor, M.²

31
- 33646515110
- (f) Movassagh, B.; Fazeli, A. Z. Naturforsch., B 2006, 61, 194.
- (2006) Z. Naturforsch., B , vol.61 , pp. 194
- Movassagh, B.¹ Fazeli, A.²

32
- 2442432436
- (g) Movassagh, B.; Shamsipoor, M.; Joshaghani, M. J. Chem. Res., Synop. 2004, 148.
- (2004) J. Chem. Res., Synop , pp. 148
- Movassagh, B.¹ Shamsipoor, M.² Joshaghani, M.³

33
- 57149127111
- (h) Movassagh, B.; Shamsipoor, M. Synlett 2005, 127.
- (2005) Synlett , pp. 127
- Movassagh, B.¹ Shamsipoor, M.²

34
- 34548483214
- (i) Movassagh, B.; Fazeli, A. Monatsh. Chem. 2007, 138, 863.
- (2007) Monatsh. Chem , vol.138 , pp. 863
- Movassagh, B.¹ Fazeli, A.²

35
- 67650040178
- General Procedure: A mixture of diaryl diselenide (0.5 mmol) and zinc powder (3.0 mmol) in anhydrous MeCN (15 mL, was stirred at 70°C. After 15 min, anhydrous AlCl3 (3.0 mmol in 2 mL anhydrous MeCN) was added cautiously. The mixture was stirred for 1 h at 70 °C, until the yellow solution turned colorless. The mono-activated cyclopropane (1.1 mmol) was then added to the solution and the mixture was stirred at 70 °C for the period of time specified in Table 1. The progress of reaction was monitored with TLC. After the reaction was complete, the solution was filtered and the solvent was evaporated. Aqueous HCl (10, was added to the crude product and the mixture was extracted with EtOAc (2 × 30 mL, The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification by preparative TLC (silica gel; n-hexane-EtOAc, 3:1) gave the corresponding arylselenenyl-f
- +, 208 (38), 141 (14), 128 (100), 115 (65),

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.