Addition of a silyl ketene acetal to alpha,beta-unsaturated cyclic anhydrides
| Title | Addition of a silyl ketene acetal to alpha,beta-unsaturated cyclic anhydrides |
| Publication Type | Journal Article |
| Year of Publication | 2010 |
| Authors | Gnaneshwar, R, Sivaram, S |
| Journal | Synthetic Communications |
| Volume | 40 |
| Issue | 16 |
| Pagination | PII 924771265 |
| Date Published | JUL |
| ISSN | 0039-7911 |
| Keywords | 1, 2-Addition, 4-addition, cyclic anhydrides, Lewis acid, Silyl ketene acetal |
| Abstract | Addition of [1-methoxy-2 methyl-1-propenyl)-oxy] trimethylsilane (MTS) to unsymmetrical ,-unsaturated cyclic anhydrides (namely, itaconic anhydride and citraconic anhydride) as well as symmetrical anhydrides (namely, maleic anhydride and 2,3-dimethylmaleic anhydride) was investigated. Itaconic anhydride isomerizes to citraconic anhydride in the presence of MTS. In the presence of Lewis acid catalysts (Yb(OTf)3/CH2Cl2), MTS adds to itaconic anhydride at room temperature in a 1,4-fashion. 1,2-Addition is the preferred pathway with both 2,3-dimethyl maleic anhydride and citraconic anhydride. |
| DOI | 10.1080/00397910903243815 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 0.937 |
Divison category:
Polymer Science & Engineering