Acid-promoted transformations of 1-(diphenylphosphoryl)allenes: synthesis of novel 1,4-dihydrophosphinoline 1-oxides
Bogachenkov, AS; Dogadina, AV; Boyarskiy, VP; Vasilyev, AV
| HERO ID | 5417274 |
|---|---|
| In Press | No |
| Year | 2015 |
| Title | Acid-promoted transformations of 1-(diphenylphosphoryl)allenes: synthesis of novel 1,4-dihydrophosphinoline 1-oxides |
| Authors | Bogachenkov, AS; Dogadina, AV; Boyarskiy, VP; Vasilyev, AV |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 13 |
| Issue | 5 |
| Page Numbers | 1333-1338 |
| Abstract | 1-(Diphenylphosphoryl)alka-1,2-dienes (phosphonoallenes) in Brønsted (super)acids (TfOH, FSO3H, and H2SO4) at -70 to 120 °C for 30 min to 4 h gave, at first, (3-hydroxyalk-1-en-1-yl)diphenylphosphine oxides, as kinetically favorable reaction products, that are further converted into 1-phenyl-1,4-dihydrophosphinoline 1-oxides as thermodynamically stable compounds. The latter compounds are formed from phosphonoallenes under the action of a strong Lewis acid AlCl3 at room temperature for 10-120 min. This is a novel, simple and efficient (short reaction time, high yields) method for synthesis of such 1,4-dihydrophosphinoline 1-oxides. |
| Doi | 10.1039/c4ob02269f |
| Pmid | 25526497 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |