Intramolecular C-H⋯O hydrogen bond controlling the conformation of heterocycles: Synthesis, structure and catalytic reactivity of aluminum aryloxides

Chia Her Lin, Liang Fu Yan, Fa Cherng Wang, Yih Lu Sun, Chu Chieh Lin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

The reactions of R2AlX with one equivalent of 2,2′-methylene-bis-(4,6-di-tert-butylphenol) (MDBP-H2) or 2,2′-methylene-bis-(4-methyl-6-tert-butylphenol) (MMBP-H2) in oxygenated solvent afford monomeric four-coordinated compounds, XAl(MDBP)(S), 1-5 (1: R = Me, X = Br, S = Et2O; 2: R = Et, X = Cl, S = Et2O; 3: R = Me, X = Br, S = THF; 4: R = Et, X = Cl, S = THF; 5: R = X = Et, S = Et2O) or XAl(MMBP)(S), 6-8 (6: R = X = Et, S = Et2O; 7: R = X = iBu, S = Et2O; 8: R = Et, X = Cl, S = Et2O). Crystal structures of 1, 2 and 7 demonstrate that the conformation of the eight-membered heterocycles containing aluminum is controlled by an unusual intramolecular C-H⋯O hydrogen bond. Et2AlCl or iBu3Al reacts with one equivalent of 2,2′-ethylidene-bis-(4,6-di-tert-butylphenol) (EDBP-H2) or MDBP-H2 in toluene giving a dimeric four coordinate compound [CLAL(μ-EDBP]2, 9 or [iBuAl(μ-MDBP)]2, 10. Some of these compounds have shown great catalytic activities toward the reaction of cyclopentadiene with methacrolein.

Original languageEnglish
Pages (from-to)151-159
Number of pages9
JournalJournal of Organometallic Chemistry
Volume587
Issue number2
DOIs
Publication statusPublished - 1999 Sep 25
Externally publishedYes

Keywords

  • Aluminum
  • Aryloxide
  • Catalysis
  • Hydrogen bond

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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