Lithium Perchlorate as a Reagent for Synthesis of Covalently Bonded Organic Perchlorates via Electrophilic Additions of Halogens and Nitronium Tetrafluoroborate to Olefins

N. S. Zefirov, A. S. Koz'min, V. V. Zhdankin, A. V. Nikulin, N. V. Zyk

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Abstract

The reaction of a series of olefins with chlorine and bromine in the presence of a large excess of lithium Perchlorate in ether gave 1,2-halo Perchlorates together with the corresponding 1,2-dihalides. Analogous reactions of NO2BF4 in the presence of LiClO4 in methylene chloride or ethyl acetate with monoolefins gave 1,2-nitro Perchlorates. Norbornadiene reacted with a NO2BF4/LiClO4 system to give two isomeric nitro Perchlorates of nortricyclenic structure. Several synthetic and mechanistic aspects of this new reaction of electrophilic perchloration of olefins are discussed.

Original languageEnglish (US)
Pages (from-to)3679-3684
Number of pages6
JournalJournal of Organic Chemistry
Volume47
Issue number19
DOIs
StatePublished - Jan 1 1982

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Perchlorates
Halogens
Alkenes
Bromine
Methylene Chloride
Chlorine
Ether
lithium perchlorate

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Lithium Perchlorate as a Reagent for Synthesis of Covalently Bonded Organic Perchlorates via Electrophilic Additions of Halogens and Nitronium Tetrafluoroborate to Olefins. / Zefirov, N. S.; Koz'min, A. S.; Zhdankin, V. V.; Nikulin, A. V.; Zyk, N. V.

In: Journal of Organic Chemistry, Vol. 47, No. 19, 01.01.1982, p. 3679-3684.

Research output: Contribution to journalArticle

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