Table 1.
Cross metathesis of 1 with methyl acrylatea.
Entry | [1] (mol·L−1) | Cat. loading (mol %) | BQb (mol %) | Conv. (%)c (yield %)d | % isom.e |
1 | 0.5 | 1 | 5 | 100 | 13 |
2 | 0.5 | 2 | 5 | 100 | 15 (18)f |
3 | 0.5 | 1 | 10 | 95 | 7.6 |
4 | 0.5 | 2 | 10 | 100 (69) | 7 |
5 | 0.25 | 2 | 10 | 95 | 8 |
6 | 1 | 2 | 10 | 100 | 10 |
7g | 0.5 | 2 | 10 | 100 | 8 |
8h | 0.5 | 2 | 10 | 90 | 11 |
a0.11 mL of 1 (1 mmol), 0.18 mL of methyl acrylate (2 mmol), BQ, DMC, catalyst, 2 h; bbenzoquinone; cdetermined by gas chromatography using dodecane as internal standard; disolated yield; edetermined by gas chromatography as ratio of ((isomerisation products)/(isomerisation products + 2)) × 100; freaction performed without benzoquinone; gin toluene; hHoveyda 2nd gen. catalyst.