C-C bond formation at ozonide rings by substitution of chlorinated ozonides

Karl Griesbaum, Ralf Olaf Quinkert, Kevin J. McCullough

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The TiCl4-mediated substitution of 3-chloro-3,5- bis(chloromethyl)-5-methyl-1,2,4-trioxolane (1) with 1-(trimethylsilyloxy) cyclopentene (4), 2-methyl-1-(trimethylsilyloxy)propene (6) and allyltrimethylsilane (12) gave the corresponding 2-oxocyclopentyl-, 1,1-dimethyl-2-oxo-ethyl- and allyl-substituted ozonides 5, 7 and 13, respectively. Substitution of 3,5-dichloro-3,5-bis(chloromethyl)-1,2,4- trioxolane (2) with allyl-trimethylsilane (12) gave the diallyl-substituted ozonide 14. Ozonolysis of the allyl-substituted ozonide 13 provided the corresponding diozonide 17, and ozonolysis of the diallyl-substituted ozonide 14 provided the corresponding diozonide 18 and triozonide 19. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Original languageEnglish
Pages (from-to)3657-3662
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
Publication statusPublished - 27 Aug 2004

Keywords

  • C-C coupling
  • Ozonolysis
  • Substitution
  • Synthetic methods

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