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Volumn 643-644, Issue , 2002, Pages 247-252

The Cl2(PCy3)(IMes)Ru(=CHPh) catalyst: Olefin metathesis versus olefin isomerization

Author keywords

Carbene; Isomerization; Metathesis; Ruthenium

Indexed keywords

ALKADIENE; ALKENE; CHLORIDE; IMIDAZOLE; RUTHENIUM; SOLVENT;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CONTROLLED STUDY; ISOMERISM; REACTION TIME; TEMPERATURE;

EID: 10344222274 PISSN: 0022328X EISSN: None Source Type: Journal
DOI: 10.1016/S0022-328X(01)01269-4 Document Type: Article

Times cited : (142)

References (27)

1
- 0002138516
- For a review on stable carbenes and their applications, see
- (2000) Chem. Rev. , vol.100 , pp. 39
- Bourissou, D.¹ Guerret, O.² Gabbaï, F.P.³ Bertrand, G.⁴

4
- 0033582991
- The synthesis of this catalyst was also reported by Grubbs:
- (1999) Tetrahedron Lett. , vol.40 , pp. 2247
- Schooll, M.¹ Trnka, T.M.² Morgan, J.P.³ Grubbs, R.H.⁴

7
- 0033598258
- 2], the unsaturated version of [RuIMes], see
- (1999) Org. Lett. , vol.1 , pp. 953
- Scholl, M.¹ Ding, S.² Lee, C.W.³ Grubbs, R.H.⁴

9
- 0033603294
- See for instance the synthesis of tetrasubstituted double bonds
- (1999) Tetrahedron Lett. , vol.40 , pp. 4787
- Ackermann, L.¹ Füstner, A.² Weskamp, T.³ Kohl, F.J.⁴ Herrmann, W.A.⁵

11
- 0034685462
- See also the synthesis of acrylate derivatives by Cross Metathesis (CM)
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 3783
- Chatterjee, A.K.¹ Morgan, J.P.² Scholl, M.G.³ Grubbs, R.H.⁴

15
- 0033582741
- RCM is very sensitive to steric hindrance, and there is no report of a successful RCM between two neo-pentylic double bonds. For a failure, see
- (1999) Tetrahedron Lett. , vol.40 , pp. 1429
- Hoye, T.R.¹ Promo, M.A.²

17
- 0034597108
- and references therein
- (2000) J. Mol. Catal. A , vol.159 , pp. 185
- Salvini, A.¹ Piacenti, F.² Frediani, P.³

18
- 0033578944
- For a study on the decomposition of [Ru] catalyst, see: The nature of the ruthenium-containing inorganic products is not known.
- (1999) J. Org. Chem. , vol.64 , pp. 7202
- Ulman, M.¹ Grubbs, R.H.²

24
- 0030994105
- For a detailed study on the RCM mechanism, see
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 3887
- Dias, E.L.¹ Nguyen, S.T.² Grubbs, R.H.³

25
- 0008492930
- However, Fürstner et al. reported an increased reaction rate for the reaction in toluene compared to the reaction in DCE (see Ref. [13]. But isomerization was negligible in DCE, and as high as 10-15% in toluene. contradiction may suggest that the polarity of the solvent is also important

26
- 0008436367
- We have also shown that a fivefold increase or a decrease of the concentration is without any influence on the outcome of the reaction, when suspecting the impurity to be the dimer resulting from cross metathesis of 1a with itself

27
- 0008525239
- This point has been extensively studied by Grubbs on the [Ru] catalyst (see Ref. [14]), and by Nolan on the [RuIMes] catalyst (see Ref. [2b])

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