35699-44-6Relevant articles and documents
Facile reductive coupling of benzylic halides with ferrous oxalate dihydrate
Khurana, Jitender M.,Chauhan, Sushma,Maikap, Golak C.
, p. 1737 - 1740 (2007/10/03)
Facile reductive coupling of benzylic halides is reported with ferrous oxalate dihydrate in DMF or HMPA under nitrogen atmosphere at 155-160°C. The coupling is proposed to proceed by two successive oxidative additions of benzylic halides to ferrous oxalate to give an intermediate organoiron complex which undergoes concerted dimerization to give the corresponding reductively coupled dimers in high yields.
Unusual triethylamine catalyzed rearrangement of bicyclic endoperoxides derived from substituted cycloheptatrienes
Senguel, M. Emin,Ceylan, Zeynep,Balci, Metin
, p. 10401 - 10408 (2007/10/03)
Triethylamine catalyzed rearrangement of the substituted bicyclic cycloheptatriene endoperoxides 9, 10, 12, 13, 20, 21, 22 and 30 underwent different reaction modes and resulted in the formation of ring contraction products in the case of 9, 10, 12 and 13. However, 20, 21, and 30 provided rearranged diketones 23, 24 and 32 almost in quantitative yield. The mechanism of these reactions was discussed.
Manganese(III)-Mediated Formylation of Aromatic Compounds in the Presence of Malonic Acid
Nishino, Hiroshi,Tsunoda, Katsunori,Kurosawa, Kazu
, p. 545 - 550 (2007/10/02)
The reaction of naphthlenes with malonic acid in the presence of manganese(III) acetate gives naphthalenecarbaldehydes and naphthalenecarboxylic acids.Similar reactions of anthracene, pyrene, and methoxybenzenes also yield formylated and carboxylated products.It was found that the formyl group introduced to the aromatic ring was not derived from carboxymethyl radical generated directly by the thermolysis of manganese(III) acetate, but from a dicarboxymethyl radical formed by the interaction of malonic acid and manganese(III) acetate.In addition, it was also found that the dicarboxymethyl radicals attacked the position of the highest electron density on the aromatic ring and that this formylation was effective when the ionization potential of the aromatic copound was lower than 7.8 eV.
ELECTRON TRANSFER ACTIVATION. HYDROPEROXIDE INTERMEDIATES IN A NOVEL AND SELECTIVE PROCEDURE FOR BENZYLIC OXIDATIONS.
Santamaria, J.,Jroundi, R.,Rigaudy, J.
, p. 4677 - 4680 (2007/10/02)
A selective and mild photochemical procedure for benzylic oxidations with 9,10-dicyanoanthracene (DCA) an usual electron acceptor, in the presence of methyl viologen (MV2+), an electron relay, has been developed.Methyl and methylene groups are oxidized in good to excellent yields to the corresponding hydroperoxides.
FORMATION OF MONOALDEHYDES BY CERIUM(IV) AMMONIUM NITRATE OXIDATION OF UNSYMMETRIC DIMETHYLNAPHTHALENES
Sydnes, Leiv K.,Hansen, Sissel H.,Burkow, Ivan C.,Saethre, Leif J.
, p. 5205 - 5208 (2007/10/02)
When 1,2-,1,3-and 1,6-dimethylnaphthalene are oxidized by Ce(4+) in acetic acid the corresponding monoaldehydes are formed in better than 80percent yield.In each case aldehyde formation takes place with a high degree of selectivity as the methyl-1-to methyl-2-naphthaldehyde ratio is better than 11:1.The selectivity may be explained from differences in reactivity as calculated within the frontier orbital method.
Ortho Metalation Directed by α-Amino Alkoxides
Comins, Daniel L.,Brown, Jack D.
, p. 1078 - 1083 (2007/10/02)
The addition of aromatic aldehydes to certain lithium dialkylamides in benzene or tetrahydrofuran gave α-amino alkoxides which were ortho lithiated with excess n-butyllithium.Subsequent alkylation and hydrolysis provided ortho-substituted aromatic aldehydes via a one-pot reaction.The ortho metalation of α-amino alkoxides derived from 1- and 2-naphthaldehyde and various substituted benzaldehydes was examined.When N,N,N'-trimethylethylenediamine was used as the amine component of the α-amino alkoxide, metalation could be carried out at lower temperatures.This rate increase is due to an intramolecular TMEDA-like assisted metalation.The synthetic utility of this ortho metalation, including how varying the amine component of the α-amino alkoxide affects the regiochemistry and metalation rate, is discussed.
PHOTOOXYGENATIONS PAR TRANSFERT D'ELECTRON SENSIBILISEES PAR LE DICYANO-9,10 ANTHRACENE. ROLE DU SOLVANT ET FORMATION D'OXYGENE SINGULET.
Santamaria, J.,Gabillet, P.,Bokobza, L.
, p. 2139 - 2142 (2007/10/02)
Photooxygenation of naphtalenic compounds sensitized by electron acceptors like 9,10 dicyanoanthracene (DCA) is shown to proceed by two distinct ways depending on the solvent polarity.In a polar solvent superoxide ion (O2-.) as well as singlet oxygen (1O2*) are involved while in a non polar solvent only singlet oxygen is produced.
