62748-42-9Relevant academic research and scientific papers
Electrochemical cleavage of double bonds in conjugated cycloalkenyl- and 1,2-alkenobenzenes
Ogibin, Yuri N.,Ilovaisky, Alexey I.,Nikishin, Gennady I.
, p. 3256 - 3258 (2007/10/03)
The electrochemical cleavage of olefinic bonds in conjugated C5-C7-cycloalkenylbenzenes 1, indene 4a, and 1,2-dihydronaphthalene (4b) results from anodic oxidation of these compounds in MeOH in an undivided cell. The process includes the formation of (1,2-dimethoxycycloalkyl)benzenes 2a-c, 1,2-dimethoxyindan (5a), and 1,2-dimethoxytetralin (5b) as intermediates and leads to ω,ω-dimethoxy-ω-phenyl-n-C5-C7-alkanal dimethyl acetals 3a-c, [2-(dimethoxymethyl)phenyl]ethanal dimethyl acetal (6a), and 3-[2-(dimethoxymethyl)phenyl]propanal dimethyl acetal (6b) as major products, respectively. The best yields of 3a-c and 6a,b (58-76%) were obtained when the electrolysis was carried out at 60°C and 6 F/mol of electricity based on 1, 4a, and 4b was passed using C-anode and Bu4NBF4 as a supporting electrolyte. Compounds 2a-c and 5a,b as mixtures of cis and trans diastereomers were obtained as major products in 81-90% yield when the electrolysis was terminated after 2 F/mol of electricity based on 1, 4a, and 4b had been passed. The cis/trans ratio in 2a-c was increased with the increasing the size of cycloalkane rings in 1, 4a, and 4b and the obvious stereoselective effect of the anode nature (C or Pt) being observed in the case of dimethoxylation of 4a.
A new approach to arylaliphatic 1,5-, 1,6-, and 1,7-dicarbonyl compounds and their monoacetals based on direct anodic oxidation of 1-phenyl- and benzo[c]cycloalkenes
Ogibin,Ilovaisky,Nikishin
, p. 1939 - 1941 (2007/10/03)
A new simple approach to ω-benzoylalkanals, 2-(ω-formylalkyl)benzaldehydes, and their monoacetals was developed based on direct anodic oxidation of 1-phenylcycloalkenes and benzo[c]cycloalkenes in methanol followed by acid hydrolysis of the electrolysis p
IODOSOBENZENE TETRAFLUOROBORATE: FIRST EXAMPLE OF A STABLE ELECTROPHILIC HYPERVALENT IODINE REAGENT WITHOUT NUCLEOPHILIC LIGANDS
Zhdankin, Viktor V.,Tykwinski, Rik,Caple, Ronald,Berglund, Bruce,Koz'min, Anatoly S.,Zefirov, Nikolai S.
, p. 3717 - 3720 (2007/10/02)
Iodosobenzene tetrafluoroborate 1 has been prepared by the reaction of PhI(OAc2) and aqueous HBF4, and its reactions with alkenes, silyl enol ethers, and acetylenes have been studied.
MERCURY(II) OXIDE/TETRAFLUOROBORIC ACIDPROMOTED VICINAL HYDROXY- AND ALKOXYLATION OF ALKENES
Barluenga, Jose,Alonso-Cires, Luisa,Campos, Pedro J.,Asensio, Gregorio
, p. 2563 - 2568 (2007/10/02)
The reaction of alkenes with mercury(II) oxide/tetrafluoroboric acid and alcohols or water involves reduction to Hg(O) and vicinal diethers or diols are produced in good yields.Olefins bearing benzylic hydrogens in an α position lead to cinnamyl ethers.Mechanisms are proposed to account for the products and their stereochemistry.
