Fused polycyclic hydrocarbons through superacid-induced cyclialkylation of aromatics
Ledneczki, I; Forgo, P; Molnar, A
HERO ID
857495
Reference Type
Journal Article
Year
2007
Language
English
| HERO ID | 857495 |
|---|---|
| In Press | No |
| Year | 2007 |
| Title | Fused polycyclic hydrocarbons through superacid-induced cyclialkylation of aromatics |
| Authors | Ledneczki, I; Forgo, P; Molnar, A |
| Journal | Catalysis Letters |
| Volume | 119 |
| Issue | 3-4 |
| Page Numbers | 296-303 |
| Abstract | Benzene and substituted derivatives (toluene, ortho-xylene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, anisole), when applied in large excess, react with 1,4 diols (pentan-1,4-diol, hexan-2,5-diol, and 2,5-dimethylhexan-2,5-diol) or an oxolane (2,2,5,5-tetramethyltetrahydrofuran) in the presence of the Bronsted superacid trifluoromethanesulfonic acid (triflic acid, TFSA) to afford substituted tetralins in excellent yields with high selectivity. Reacting benzene with a small excess of alkylating agents yields octahydroanthracenes. The transformation of naphthalene with oxolane leads to a partially saturated octamethyloctahydrotetracene under similar conditions. Product formation is interpreted by intermolecular Friedel-Crafts alkylation followed by cyclialkylative ring closure. |
| Doi | 10.1007/s10562-007-9234-2 |
| Wosid | WOS:000250996200016 |
| Url | <Go to ISI>://WOS:000250996200016 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Keyword | alkylation; cyclialkylation; arenes; carbocations; superacid; chemistry, physical |
| Is Qa | No |