C−C Bond Formation at Ozonide Rings by Substitution of Chlorinated Ozonides

Medientyp: E-Artikel
Titel: C−C Bond Formation at Ozonide Rings by Substitution of Chlorinated Ozonides
Beteiligte: Griesbaum, Karl; Quinkert, Ralf‐Olaf; McCullough, Kevin J.
Erschienen: Wiley, 2004
Erschienen in: European Journal of Organic Chemistry, 2004 (2004) 17, Seite 3657-3662
Sprache: Englisch
DOI: 10.1002/ejoc.200400167
ISSN: 1099-0690; 1434-193X
Schlagwörter: Organic Chemistry ; Physical and Theoretical Chemistry
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Beschreibung: AbstractThe 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 allyltrimethylsilane (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)

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