81971-84-8Relevant academic research and scientific papers
OXIDATIVE ADDITION OF ANIONS TO ALKENES BY THE ACTION OF COMPOUNDS OF TETRAVALENT LEAD IN THE PRESENCE OF CHLORIDE ION IN AN ACIDIC MEDIUM
Serguchev, Yu. A.,Gutsulyak, R. B.
, p. 1784 - 1790 (2007/10/02)
In the reaction of alkenes (cyclohexene, 1-hexene, styrene) with compounds of tetravalent lead in various acids (trifluoroacetic, acetic, methanesulfonic, perchloric) in the presence of metal chlorides the joint addition of the chloride anion and the anion of the respective acids to the alkenes takes place with a high degree of selectivity, leading to the formation of vicinal bifunctional derivatives of alkanes.The effectiveness of the addition of the anions of the acids to the alkenes under the given conditions varies directly with the strength of the acid and inversely with the nucleophilicity and the basicity of its anion.A new convenient method is proposed for the oxidative chlorofluorination of cyclohexene in aqueous hydrofluoric acid.
NOVEL METHOD OF DEOXIDATION OF ALCOHOLS AND ITS USE IN SYNTHESIS OF COVALENT PERCHLORATES
Zefirov, Nikolai S.,Zhdankin, Viktor V.,Sorokin, Viktor D.,Koz'min, Anatoly S.
, p. 6243 - 6244 (2007/10/02)
Alcohols can be effectively deoxidated by treatment with chlorine and sulfur in the presence of pyridine with incorporation of an external nucleophile from added salts.
Oxidatively Assisted Nucleophic Substitution of Iodine in Alkyl Iodides by Nucleofugic Anions
Zefirow, Nikolai S.,Zhdankin, Victor V.,Makhon'kova, Galina V.,Dan'kov, Yuri V.,Koz'min, Anatoly S.
, p. 1872 - 1876 (2007/10/02)
The reaction of alkyl iodides with chlorine or nitronium tetrafluoroborate in the presence of salts of perchloric or substitued sulfonic acids gave alkyl perchlorates or sulfonates as principal products.Some mechanistic aspects of this new reaction are discussed.
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.
, p. 3679 - 3684 (2007/10/02)
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 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.
