1003-17-4Relevant articles and documents
Oxygen Transfer by Dialkylperoxonium Ions
Bloodworth, A. J.,Melvin, T.,Mitchell, John C.
, p. 2612 - 2613 (1986)
Oxygen-transfer from dialkylperoxonium ions R2O+OH has been demonstrated for three such species, where R2 is a hydrocarbon chain or ring, by oxidation of several dialkyl sulfoxides, methyl phenyl sulfide, and the succinimide anion, with concurrent formation of the corresponding cyclic or bicyclic ether R2O.
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Sneen,R.A.,Matheny,N.P.
, p. 3905 - 3906 (1964)
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Rule of five cyclizations in 5-hexenyl radicals and photocycloadditions of 1,5-hexadienes: Effect of 4-oxa substitution
Matlin, Albert R.,Brinton, Karen Feit,Nivaggioli, Belinda Tsao
, p. 83 - 87 (2007)
The effect of 4-oxa substitution on the regiochemistry and rate of 5-hexenyl radical cyclizations was investigated, as a potential model for [2 + 2] photocycloadditions of 2-acyl-4-oxa-1,5-hexadienes. Increasing the electron density in the alkene decreases the rate of cyclization in the 4-oxa-hexejiyl radicals, relative to the all carbon analogs, but has little effect on the regioselectivity of the cyclization. The radical model does not reproduce the high degree of 1,6 closure, observed in the [2 + 2] photocycloadditions for 4-oxa-1,5-hexadiene la. However, the radical model does reinforce the interpretation that ground state conformational effects, engendered by substitution remote from the reacting centers have important rate consequences for cyclization reactions. Copyright
Cyclization of 4-Hydroxy-4-methyl-1-pentyl p-Toluenesulfonate as a Model to Evaluate Inherent Medium Effect on SN2 Solvolysis
Shimizu, Nobujiro,Tsutsumi, Toru,Tsuno, Yuho
, p. 2065 - 2068 (1991)
Solvent effect on the cyclization of 4-hydroxy-4-methyl-1-pentyl p-toluenesulfonate, a mechanistic equivalent to the SN2 solvolysis, was successfully analyzed by Taft LSER equation as log k=3.2?*+1.4α+1.9β-8.36, indicating that three independent factors are operative, i.e., solvent polarity and H-bond donor ability which promote ionization, and H-bond acceptor ability which enhances nucleophilicity of the internal OH group.
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Walling,C.,Padwa,A.
, p. 1597 - 1601 (1963)
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METHOD FOR PREPARING TRIOLS AND DIOLS FROM BIOMASS-DERIVED REACTANTS
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Paragraph 0092; 0093, (2014/09/30)
A method to make triols and diols is described. The method includes the steps of performing an aqueous-phase hydrodeoxygenation reaction on a feedstock containing a biomass-derived reactant in aqueous solution. The feedstock is contacted with a heterogeneous metal-containing bifunctional catalyst or a combination of two or more heterogeneous metal-containing catalysts that catalyze cleavage of C—C and C—O bonds, for a time, temperature, pressure, and weight hourly space velocity to yield a product mix comprising triols, diols, or combinations thereof.
Calcium catalyzed hydroalkoxylation
Kena Diba, Anastasie,Begouin, Jeanne-Marie,Niggemann, Meike
supporting information, p. 6629 - 6632,4 (2012/12/13)
A calcium catalyzed intramolecular hydroalkoxylation reaction is presented, as a transition metal free, inexpensive, and very mild process for the highly atom economic formation of cyclic ethers from γ,δ-unsaturated alcohols. In contrast to most of the previously reported procedures, room temperature conditions are fully sufficient in most cases for a high yielding cycloisomerization in the presence of a combination of 5 mol-% Ca(NTf 2)2 and 5 mol-% Bu4NPF6. Full regioselectivity is observed in all transformations.
