Alkylation of aromatics with diols in superacidic media

Árpád Molnár, Béla Török, I. Bucsi, Andrea Földvári

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Friedel-Crafts alkylation of simple aromatics (benzene, toluene, o-, m- and p-xylene) with various types of diols in the presence of superacidic trifluoromethanesulfonic acid was studied. 1,2- and 1,3-diols were found to bring about only monoalkylation yielding unusual monoalkylated products: bis(1-methyl-2-phenylpropyl) ether was formed in the reaction of 2,3-butanediol, and 2,4-dimethyl-2,4-pentanediol produced mono- and di-tert-butyl-substituted benzenes. Higher diol homologues, in turn, undergo electrophilic cyclialkylative ring closure (cyclialkylation) to form tetralin derivatives with high selectivities and in good yields. Additional primary alkylation processes are monoalkylation to yield alkylbenzenes and the formation of diphenylalkanes. The products thus formed may participate in secondary transformations, which are a second cyclialkylation (formation of octahydroanthracene and -phenanthrene derivatives), isomerization and dehydrogenation. Mechanistic studies with stereoisomeric 2,5-hexanediols point to the involvement of open dicationic intermediates in the alkylation process.

Original languageEnglish
Pages (from-to)9-16
Number of pages8
JournalTopics in Catalysis
Volume6
Issue number1-4
Publication statusPublished - 1998

Fingerprint

alkylation
Alkylation
Benzene
benzene
Derivatives
phenanthrene
Toluene
xylene
Dehydrogenation
Xylene
products
dehydrogenation
Isomerization
Ether
isomerization
closures
toluene
Ethers
ethers
vehicles

Keywords

  • Benzene
  • Cyclialkylation
  • Dicationic intermediates
  • Diols
  • Friedel-Crafts alkylation
  • Methylbenzenes
  • Tetralin derivatives
  • Triflic acid

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (miscellaneous)
  • Physical and Theoretical Chemistry

Cite this

Molnár, Á., Török, B., Bucsi, I., & Földvári, A. (1998). Alkylation of aromatics with diols in superacidic media. Topics in Catalysis, 6(1-4), 9-16.

Alkylation of aromatics with diols in superacidic media. / Molnár, Árpád; Török, Béla; Bucsi, I.; Földvári, Andrea.

In: Topics in Catalysis, Vol. 6, No. 1-4, 1998, p. 9-16.

Research output: Contribution to journalArticle

Molnár, Á, Török, B, Bucsi, I & Földvári, A 1998, 'Alkylation of aromatics with diols in superacidic media', Topics in Catalysis, vol. 6, no. 1-4, pp. 9-16.
Molnár Á, Török B, Bucsi I, Földvári A. Alkylation of aromatics with diols in superacidic media. Topics in Catalysis. 1998;6(1-4):9-16.
Molnár, Árpád ; Török, Béla ; Bucsi, I. ; Földvári, Andrea. / Alkylation of aromatics with diols in superacidic media. In: Topics in Catalysis. 1998 ; Vol. 6, No. 1-4. pp. 9-16.
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