Reactions of some alken-1-yl and cycloalken-1-yl bromomethyl sulfones with dimethyl malonate and malononitrile
Vasin, VA; Bolusheva, IYu; Razin, VV
| HERO ID | 4936164 |
|---|---|
| In Press | No |
| Year | 2012 |
| Title | Reactions of some alken-1-yl and cycloalken-1-yl bromomethyl sulfones with dimethyl malonate and malononitrile |
| Authors | Vasin, VA; Bolusheva, IYu; Razin, VV |
| Journal | Russian Journal of Organic Chemistry |
| Volume | 48 |
| Issue | 9 |
| Page Numbers | 1173-1179 |
| Abstract | Bromomethyl cyclopent-1-enyl sulfone and bromomethyl cyclohex-1-enyl sulfone reacted with dimethyl malonate and malononitrile sodium salts in THF at 20-50A degrees C to give products of Michael-induced Ramberg-Backlund reaction, functionalized derivatives of methylidenecyclopentane and methylidenecyclohexane. Reactions of bromomethyl hex-1-en-1-yl sulfone and bromomethyl hept-1-en-1-yl sulfones with the same sodium enolates followed the Michael-induced ring closure pattern with formation of tetrahydrothiophene 1,1-dioxide derivatives containing allylmalonic acid derivatives as impurities. Factors responsible for the different reaction pathways of cyclic and acyclic bromomethyl sulfones are discussed. |
| Doi | 10.1134/S1070428012090047 |
| Wosid | WOS:000309724000004 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |