π-conjugated conjoined double helicene via a sequence of three oxidative CC- and NN-homocouplings

Kouichi Shiraishi, Andrzej Rajca, Maren Pink, Suchada Rajca

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

Dimerization of planarized diamine 2 using benzoyl peroxide gave dihydrazine 1 in about 70% yield; that is, three dehydrogenations (one CC- and two NN-homocouplings) and two ring closures were attained in one synthetic step. Dihydrazine 1 may be viewed as a chiral π-conjugated conjoined double helicene, with two homochiral [5]helicene-like fragments, annelated in their mid-sections. A relatively high barrier of 35 kcal mol-1 for inversion of configuration for one of the [5]helicene-like helices in 1 was found.

Original languageEnglish (US)
Pages (from-to)9312-9313
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number26
DOIs
StatePublished - Jul 6 2005

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Benzoyl Peroxide
Benzoyl peroxide
Diamines
Dimerization
Dehydrogenation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

π-conjugated conjoined double helicene via a sequence of three oxidative CC- and NN-homocouplings. / Shiraishi, Kouichi; Rajca, Andrzej; Pink, Maren; Rajca, Suchada.

In: Journal of the American Chemical Society, Vol. 127, No. 26, 06.07.2005, p. 9312-9313.

Research output: Contribution to journalArticle

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