Fused polycyclic hydrocarbons through superacid-induced cyclialkylation of aromatics

István Ledneczki, P. Forgó, Árpád Molnár

Research output: Contribution to journalArticle

2 Citations (Scopus)

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 Brønsted 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.

Original languageEnglish
Pages (from-to)296-303
Number of pages8
JournalCatalysis Letters
Volume119
Issue number3-4
DOIs
Publication statusPublished - Dec 2007

Fingerprint

Cyclic Hydrocarbons
Benzene
Tetrahydronaphthalenes
hydrocarbons
Hydrocarbons
benzene
anisole
acids
Acids
Alkylating Agents
alkylation
Alkylation
Toluene
xylene
Xylene
Naphthalene
naphthalene
closures
toluene
vehicles

Keywords

  • Alkylation
  • Arenes
  • Carbocations
  • Cyclialkylation
  • Superacid

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Fused polycyclic hydrocarbons through superacid-induced cyclialkylation of aromatics. / Ledneczki, István; Forgó, P.; Molnár, Árpád.

In: Catalysis Letters, Vol. 119, No. 3-4, 12.2007, p. 296-303.

Research output: Contribution to journalArticle

Ledneczki, István ; Forgó, P. ; Molnár, Árpád. / Fused polycyclic hydrocarbons through superacid-induced cyclialkylation of aromatics. In: Catalysis Letters. 2007 ; Vol. 119, No. 3-4. pp. 296-303.
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