Olefin Metathesis

Schematic representation of the Olefin Metathesis.

Mechanism of the Olefin Metathesis

Mechanism of the Olefin Metathesis

Original publication	U.S. Patent 2721189. 1955, 0, 0. Angew. Chem.. 1955, 67, 426. Macromol. Chem. Phys.. 1971, 141, 161. J. Am. Chem. Soc.. 1972, 94, 2538. J. Am. Chem. Soc.. 1979, 101, 4558. Org. Lett.. 2016, 18, 2592.
Reviews	Angew. Chem. Int. Ed.. 1997, 36, 2036. Angew. Chem. Int. Ed.. 2000, 39, 3012. Arkivoc. 2005, 10, 105. Chem. Rev.. 2004, 104, 2239. Chem. Rev.. 2004, 104, 2199. Chem. Rev.. 2009, 109, 3743. J. Mol. Cat. A. 1998, 133, 1. New J. Chem.. 2005, 29, 42. Tetrahedron. 1998, 54, 4413.

Sample reactions

intermediate structure

Grubbs catalyst (1st gen.), C2H4

1 atm

CH2Cl2

RT, 12 h, 93%

intermediate structure

intermediate structure

Grubbs catalyst (1st gen.)

CH2Cl2

Reflux, 8 h

intermediate structure

intermediate structure

Grubbs catalyst (1st gen.)

CH2Cl2

Reflux, 5.5 h, 89%

intermediate structure

intermediate structure

Grubbs catalyst (1st gen.)

CH2Cl2

RT, ON, 90%

intermediate structure

intermediate structure

Grubbs catalyst (1st gen.)

CH2Cl2

RT, , 99%

intermediate structure

intermediate structure

intermediate structure

Grubbs catalyst (2nd gen.)

CH2Cl2

40 °C, 60 h, 56%

intermediate structure

intermediate structure

Grubbs catalyst (1st gen.)

CH2Cl2

Reflux, 2 h

intermediate structure

intermediate structure

Grubbs catalyst (2nd gen.)

CH2Cl2

RT, 4 h, 86%

intermediate structure

intermediate structure

C2H4, Grubbs catalyst (2nd gen.)

CH2Cl2

RT, 12 h, 98%

intermediate structure

intermediate structure

Grubbs-Hoveyda catalyst (2nd gen.)

PhMe

RT, 30 h, 76%

intermediate structure

intermediate structure

Acrolein, Grubbs-Hoveyda catalyst (2nd gen.)

CH2Cl2

RT, 2 h, 84%

intermediate structure

intermediate structure

Grubbs-Hoveyda catalyst (2nd gen.)

µW

CH2Cl2

75 °C, 30 min, 86%

intermediate structure

intermediate structure

Grubbs-Hoveyda catalyst (2nd gen.)

PhH

80 °C, 24 h

intermediate structure

intermediate structure

intermediate structure

Grubbs-Hoveyda catalyst (2nd gen.)

CH2Cl2

40 °C, 72 h, 74%

intermediate structure

intermediate structure

Methyl acrylate, Grubbs-Hoveyda catalyst (2nd gen.)

PhMe

70 °C, , 75%

intermediate structure

intermediate structure

Grubbs catalyst (1st gen.), C2H4

PhMe

RT, 24 h, 30%

intermediate structure

intermediate structure

Grubbs catalyst (1st gen.)

CH2Cl2

RT, 15 min

intermediate structure

intermediate structure

Grubbs catalyst (2nd gen.)

CH2Cl2

Reflux, 2 h, 74%

intermediate structure

intermediate structure

PhH

RT, 1 h, 92%

intermediate structure

intermediate structure

Grubbs-Hoveyda catalyst (3rd gen.)

PhH

Reflux, 20 h

intermediate structure

intermediate structure

Grubbs catalyst (2nd gen.)

CH2Cl2

Reflux, 48 h, 99%

intermediate structure

intermediate structure

Grubbs catalyst (2nd gen.)

CH2Cl2

35 °C, 60 min, 80%

intermediate structure

intermediate structure

Grubbs catalyst (2nd gen.)

20 mol%

CH2Cl2

reflux, 16.5 h, 62%

intermediate structure