The preparation of helical cyclophanes containing five-membered rings

Assunta Marrocchi, Lucio Minuti, Aldo Taticchi, Ina Dix, Henning Hopf, E. Gács-Baitz, Peter G. Jones

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Cycloadditions between the indenone derivatives prepared in situ from the bromides 12a and 12b and 4-vinyl[2.2]paracyclophane (11) yielded the Diels-Alder adducts 13a and 13b in acceptable yields. When these were heated in the presence of DDQ in toluene, the fluorenophanes 14a and 14b were produced in good yields. The diol 17 obtained from the tetralonophane 15 on treatment with POCl3/pyridine was dehydrated to the diene 18, which could be trapped by pbenzoquinone (19) to provide the cycloadducts 20 and 21; the former was oxidized to the latter by DDQ treatment. Although the even more highly annelated helical phane system 22 could be prepared from 17 and 12a, its aromatization to the ketone 24 or the hydrocarbon 25 failed. All new compounds were characterized by their spectroscopic data, in particular by extensive NMR investigations. A single-crystal X-ray structure analysis for the parent hydrocarbon phenanthreno[2.2]paracyclophane (5) is reported.

Original languageEnglish
Pages (from-to)4259-4268
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number22
Publication statusPublished - Nov 2001

Fingerprint

Hydrocarbons
Aromatization
Cycloaddition
Cycloaddition Reaction
Toluene
Ketones
Bromides
Nuclear magnetic resonance
X-Rays
Single crystals
Derivatives
X rays
(2.2)paracyclophane
pyridine

Keywords

  • Cycloadditions
  • Cyclophanes
  • Helical structures
  • Novel dienes
  • Polycyclic aromatic hydrocarbons (PAHs)

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Marrocchi, A., Minuti, L., Taticchi, A., Dix, I., Hopf, H., Gács-Baitz, E., & Jones, P. G. (2001). The preparation of helical cyclophanes containing five-membered rings. European Journal of Organic Chemistry, (22), 4259-4268.

The preparation of helical cyclophanes containing five-membered rings. / Marrocchi, Assunta; Minuti, Lucio; Taticchi, Aldo; Dix, Ina; Hopf, Henning; Gács-Baitz, E.; Jones, Peter G.

In: European Journal of Organic Chemistry, No. 22, 11.2001, p. 4259-4268.

Research output: Contribution to journalArticle

Marrocchi, A, Minuti, L, Taticchi, A, Dix, I, Hopf, H, Gács-Baitz, E & Jones, PG 2001, 'The preparation of helical cyclophanes containing five-membered rings', European Journal of Organic Chemistry, no. 22, pp. 4259-4268.
Marrocchi A, Minuti L, Taticchi A, Dix I, Hopf H, Gács-Baitz E et al. The preparation of helical cyclophanes containing five-membered rings. European Journal of Organic Chemistry. 2001 Nov;(22):4259-4268.
Marrocchi, Assunta ; Minuti, Lucio ; Taticchi, Aldo ; Dix, Ina ; Hopf, Henning ; Gács-Baitz, E. ; Jones, Peter G. / The preparation of helical cyclophanes containing five-membered rings. In: European Journal of Organic Chemistry. 2001 ; No. 22. pp. 4259-4268.
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