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Chemical Communications

Volumn , Issue 16, 2009, Pages 2142-2144

Unexpected nucleophilic behaviour of free-radicals generated from α-iodoketones

(5) De Dobbeleer, Corinne a Pospíil, Jií a De Vleeschouwer, Freija b De Proft, Frank b Markó, István E a

a UNIVERSITÉ CATHOLIQUE DE LOUVAIN (Belgium)

b VRIJE UNIVERSITEIT BRUSSEL (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL; KETONE DERIVATIVE; NUCLEOPHILE; TIN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE;

EID: 64549086419 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b901943j Document Type: Article

Times cited : (18)

References (36)

1
- 0004269715
- Recent reviews about radical chemistry in P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim
- Recent reviews about radical chemistry in: Radicals in Organic Synthesis, ed., P. Renaud, and, M. P. Sibi, Wiley-VCH, Weinheim, 2001, vol. 2
- (2001) Radicals in Organic Synthesis, Ed.

2
- 0344667717
- A. Gansauer T. Lauterbach S. Narayan Angew. Chem., Int. Ed. 2003 42 5556
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5556
- Gansauer, A.¹ Lauterbach, T.² Narayan, S.³

3
- 0036250217
- H. Yorimitsu H. Shinokubo K. Oshima Synlett 2002 674
- (2002) Synlett , pp. 674
- Yorimitsu, H.¹ Shinokubo, H.² Oshima, K.³

4
- 0032960346
- M. P. Sibi N. A. Porter Acc. Chem. Res. 1999 32 163
- (1999) Acc. Chem. Res. , vol.32 , pp. 163
- Sibi, M.P.¹ Porter, N.A.²

5
- 18144379853
- C. De Dobbeleer A. Ates I. E. Markó Tetrahedron Lett. 2005 46 3889
- (2005) Tetrahedron Lett. , vol.46 , pp. 3889
- De Dobbeleer, C.¹ Ates, A.² Markó, I.E.³

6
- 0032789966
- I. E. Markó A. Ates Synlett 1999 7 1033
- (1999) Synlett , vol.7 , pp. 1033
- Markó, I.E.¹ Ates, A.²

7
- 0025279957
- C.-K. Sha T. S. Jean D. C. Wang Tetrahedron Lett. 1990 31 3745
- (1990) Tetrahedron Lett. , vol.31 , pp. 3745
- Sha, C.-K.¹ Jean, T.S.² Wang, D.C.³

8
- 0011203974
- C. K. Sha K. C. Santhosh C.-T. Tseng C.-T. Lin Chem. Commun. 1998 397
- (1998) Chem. Commun. , pp. 397
- Sha, C.K.¹ Santhosh, K.C.² Tseng, C.-T.³ Lin, C.-T.⁴

9
- 0033610458
- C.-K. Sha F.-K. Lee C.-J. Chang J. Am. Chem. Soc. 1999 121 9875
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 9875
- Sha, C.-K.¹ Lee, F.-K.² Chang, C.-J.³

10
- 0142227940
- C.-K. Sha H.-W. Liao P.-C. Cheng S.-C. Yen J. Org. Chem. 2003 68 8704
- (2003) J. Org. Chem. , vol.68 , pp. 8704
- Sha, C.-K.¹ Liao, H.-W.² Cheng, P.-C.³ Yen, S.-C.⁴

11
- 30544447838
- H.-H. Lin G.-I. Lin Y.-R. Lin C.-F. Liang C.-H. Chen C.-K. Sha Tetrahedron Lett. 2006 47 1167
- (2006) Tetrahedron Lett. , vol.47 , pp. 1167
- Lin, H.-H.¹ Lin, G.-I.² Lin, Y.-R.³ Liang, C.-F.⁴ Chen, C.-H.⁵ Sha, C.-K.⁶

12
- 34548187489
- Although ketone functions have been reported as an efficient stabilizing group for radicals, the subsequent addition of α-keto radicals has seldom been reported. Huang states that "ketones do not add homolytically to olefins generally"
- C.-H. Jiang A. Bhattacharyya C.-K. Sha Org. Lett. 2007 9 3241
- (2007) Org. Lett. , vol.9 , pp. 3241
- Jiang, C.-H.¹ Bhattacharyya, A.² Sha, C.-K.³

13
- 64549121997
- Edvard Arnold, London, p. 153). In contrast, Nikishin describes the addition of cyclopentanone to 1-decene, in the presence of TBHP, with up to 78% yield
- R. L. Huang, S. H. Goh and S. H. Ong, in The Chemistry of Radicals, Edvard Arnold, London, 1974, p. 153
- (1974) The Chemistry of Radicals
- Huang, R.L.¹ Goh, S.H.² Ong In, S.H.³

14
- 64549093334
- G. I. Nikishin G. V. Somov A. D. Petrov Izvest. Akad. Nauk. 1961 2065
- (1961) Izvest. Akad. Nauk. , pp. 2065
- Nikishin, G.I.¹ Somov, G.V.² Petrov, A.D.³

15
- 0004269715
- P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim, p. 360
- L. C. Stella and J. N. Harvey, in Radicals in Organic Synthesis, ed., P. Renaud, and, M. P. Sibi, Wiley-VCH, Weinheim, 2001, vol. 2, p. 360
- (2001) Radicals in Organic Synthesis, Ed.
- Stella, L.C.¹ Harvey In, J.N.²

16
- 0003787137
- Wiley, New York, For selected examples, see Table S-1 For the reaction optimization, see Table S-2 For the use of Et as a radical chain promoter see:
- I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976
- (1976) Frontier Orbitals and Organic Chemical Reactions
- Fleming, I.¹

17
- 0005348332
- F. Bertrand F. Le Guyader L. Liguori G. Ouvry B. Quiclet-Sire S. Seguin S. Z. Zard C. R. Acad. Sci. 2001 4 547
- (2001) C. R. Acad. Sci. , vol.4 , pp. 547
- Bertrand, F.¹ Le Guyader, F.² Liguori, L.³ Ouvry, G.⁴ Quiclet-Sire, B.⁵ Seguin, S.⁶ Zard, S.Z.⁷

18
- 0037009039
- S. Kim C. J. Lim Angew. Chem., Int. Ed. 2002 41 3265
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3265
- Kim, S.¹ Lim, C.J.²

19
- 21344488132
- For the reaction optimization see Table S-3 Recent examples:
- M. P. Bertrand Org. Prep. Proced. Int. 1994 26 257
- (1994) Org. Prep. Proced. Int. , vol.26 , pp. 257
- Bertrand, M.P.¹

20
- 34249830143
- D. S. Masterson J. P. Shackleford Synlett 2007 1302
- (2007) Synlett , pp. 1302
- Masterson, D.S.¹ Shackleford, J.P.²

21
- 33749007994
- J. Y. Lee Y.-T. Hong S. Kim Angew. Chem., Int. Ed. 2006 45 6182
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 6182
- Lee, J.Y.¹ Hong, Y.-T.² Kim, S.³

22
- 7244257482
- S. Kim C. J. Lim Angew. Chem., Int. Ed. 2004 43 5378
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 5378
- Kim, S.¹ Lim, C.J.²

23
- 0040942563
- R. G. Parr L. Von Szentpaly S. Liu J. Am. Chem. Soc. 1999 121 1922
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 1922
- Parr, R.G.¹ Von Szentpaly, L.² Liu, S.³

24
- 33745756260
- P. K. Chattaraj U. Sarkar D. R. Roy Chem. Rev. 2006 106 2065
- (2006) Chem. Rev. , vol.106 , pp. 2065
- Chattaraj, P.K.¹ Sarkar, U.² Roy, D.R.³

25
- 0000189651
- A. D. Becke J. Chem. Phys. 1993 98 5648
- (1993) J. Chem. Phys. , vol.98 , pp. 5648
- Becke, A.D.¹

26
- 0345491105
- C. Lee W. Yang R. G. Parr Phys. Rev. B: Condens. Matter Mater. Phys. 1988 37 785
- (1988) Phys. Rev. B: Condens. Matter Mater. Phys. , vol.37 , pp. 785
- Lee, C.¹ Yang, W.² Parr, R.G.³

27
- 33751157732
- For a detailed account of these types of basis sets, see e.g.
- P. J. Stephens F. J. Devlin C. F. Chabalowski M. J. Frisch J. Phys. Chem. 1994 98 11623
- (1994) J. Phys. Chem. , vol.98 , pp. 11623
- Stephens, P.J.¹ Devlin, F.J.² Chabalowski, C.F.³ Frisch, M.J.⁴

28
- 84873055189
- Wiley, New York
- W. J. Hehre, L. Radom, P. v. R. Schleyer and J. A. Pople, Ab initio Molecular Orbital Theory, Wiley, New York, 1986
- (1986) Ab Initio Molecular Orbital Theory
- Hehre, W.J.¹ Radom, L.² Schleyer, V.P.R.³ Pople, J.A.⁴

29
- 11244282931
- Gaussian, Inc., Wallingford, CT
- M. J. Frisch et al., GAUSSIAN 03 (Revision D.01), Gaussian, Inc., Wallingford, CT, 2004
- (2004) GAUSSIAN 03 (Revision D.01)
- Frisch, M.J.¹

30
- 44449171347
- F. De Vleeschouwer V. Van Speybroeck M. Waroquier P. Geerlings F. De Proft Org. Lett. 2007 9 2721
- (2007) Org. Lett. , vol.9 , pp. 2721
- De Vleeschouwer, F.¹ Van Speybroeck, V.² Waroquier, M.³ Geerlings, P.⁴ De Proft, F.⁵

31
- 36148995600
- A. E. Reed R. B. Weinstock F. A. Weinhold J. Chem. Phys. 1985 83 735
- (1985) J. Chem. Phys. , vol.83 , pp. 735
- Reed, A.E.¹ Weinstock, R.B.² Weinhold, F.A.³

32
- 0011083499
- A. E. Reed L. A. Curtiss F. Weinhold Chem. Rev. 1988 88 899
- (1988) Chem. Rev. , vol.88 , pp. 899
- Reed, A.E.¹ Curtiss, L.A.² Weinhold, F.³

33
- 0000599369
- For reviews on the preparation of spirocyclic compounds, see:
- E. Ghera T. Yechezkel A. Hassner J. Org. Chem. 1990 55 5977
- (1990) J. Org. Chem. , vol.55 , pp. 5977
- Ghera, E.¹ Yechezkel, T.² Hassner, A.³

34
- 0033597970
- M. Sannigrahi Tetrahedron 1999 55 9007
- (1999) Tetrahedron , vol.55 , pp. 9007
- Sannigrahi, M.¹

35
- 0016186681
- J. A. Marshall S. F. Brady N. H. Andersen Fortschr. Chem. Org. Naturst. 1974 31 283
- (1974) Fortschr. Chem. Org. Naturst. , vol.31 , pp. 283
- Marshall, J.A.¹ Brady, S.F.² Andersen, N.H.³

36
- 5444250041
- N. Maulide J.-C. Vanherck I. E. Markó Eur. J. Org. Chem. 2004 3962
- (2004) Eur. J. Org. Chem. , pp. 3962
- Maulide, N.¹ Vanherck, J.-C.² Markó, I.E.³

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