HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylacetylene → Dimethyl 2,3-dimethyl-2-cyclopropene-1,1-dicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylacetylene | HCID 10419 | — |
| Reactant | 2-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olate | HCID 547673 | — |
| Catalyst | Mercury | HCID 23931 | — |
| Solvent | Hexafluorobenzene | HCID 9805 | — |
| Product | Dimethyl 2,3-dimethyl-2-cyclopropene-1,1-dicarboxylate | HCID 19096835 | 46.2% |
Reaction Steps
A nitrogen-degassed solution of 33.5 grams (0.69 mole) of 2-butyne and 20.0 grams (0.13 mole) of dimethyl diazomalonate in approximately 325 grams of hexafluorobenzene was photolyzed for approximately 100 hours, at 0° C.-5° C., employing a 100-watt Hanovia mercury lamp in a manner similar to that described in Example XCVI Part A. Similar workup of the reaction mixture afforded 10.8 grams (0.06 mole) of dimethyl 2,3-dimethyl-2-cyclopropene-1,1-dicarboxylate. NMR analysis of the product indicated the following:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05292937 |
| Source dataset | uspto-grants-1994_03 |
| ORD ID | ord-7456c4302f8c4d1c820cddec652ef071 |
| Source note | uspto-grants-1994_03 |