72390-19-3Relevant academic research and scientific papers
Saccharin sulfonic acid catalyzed N-Boc protection of amines and formation of tertbutyl ethers from alcohols
Shirini,Zolfigol,AbediniM.
experimental part, p. 603 - 607 (2010/10/21)
Saccharin sulfonic acid (SaSA), as a stable reagent is easily prepared by the reaction of saccharin with neat chlorosulfonic acid at room temperature. This compound is able to catalyze conversion of amines to their corresponding N-Boc protected amines with (Boc)2O. Alcohols were also converted to their corresponding tert-butyl ethers. All reactions took place under mild conditions giving the desired products in good to high yields.
HYDROXYMETHYLBORON COMPOUNDS
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Page/Page column 36, (2010/11/29)
The present invention provides compounds which are useful as safe substitutes for the organotin reagent used in coupling reaction for the oxymethylation of aromatic rings, such as alkoxymethylation or hydroxymethylation, with a palladium catalyst and which can dispense with chromatographic purification with silica gel in the production and are suitable for mass production; and compounds applicable even to the oxymethylation of aromatic ring substrates which do not permit coupling reaction by conventional technique or have low reactivity.
Photochemistry of phosphate esters: An efficient method for the generation of electrophiles
Givens, Richard S.,Matuszewski, Bogdan,Athey, Phillip S.,Robert Stoner
, p. 6016 - 6021 (2007/10/02)
The photochemical cleavage of benzyl diethyl phosphates, 1a-g, has been examined in tert-butyl alcohol, which produces the corresponding benzyl tert-butyl ether as the major solvolysis product upon direct irradiation. The multiplicity of the reactive excited state has been established as the singlet state. Evidence favoring an intermediate benzyl cation-phosphate ion pair formed from photofragmentation includes oxygen-18 scrambling, racemization of chiral benzyl phosphates, and substituent effects on the rate of reaction. The existence of an electrophilic intermediate is further supported by a linear free energy relationship for the rate of disappearance of 1, kdis, with Hammett σ, which gave a ρ value of -0.90 and for the rate of appearance of 2, kapp, a Hammett ρ value of -0.97. Possible mechanisms including an electron transfer either before or after homolysis or simple heterolysis of the ester bond are evaluated.
Reactivity of Aryl Vinyl Di-?-methane Systems. Mechanistic and Exploratory Organic Photochemistry
Zimmerman, Howard E.,Swafford, Richard L.
, p. 3069 - 3083 (2007/10/02)
The di-?-methane rearrangement of a series of meta and para substituted arylvinylmethane reactants was investigated with the aim of determiningthe patterns of reactivity in systems in which initial excitation is localized in the aryl moiety.Thus the photo
Photochemical Transformations. 30. Photosolvolysis of Benzyl Chlorides in tert-Butyl Alcohol. 2. Nature of Excited States
Cristol, Stanley J.,Bindel, Thomas H.
, p. 7287 - 7293 (2007/10/02)
The photosolvolysis of a number of benzyl chlorides in tert-butyl alcohol, both as a result of direct irradiation and ketone triplet sensitization, has been studied.A variety of sensitization and quenching techniques have been used.The results obtained are rationalized by the assumption that there are two triplet states of the benzyl chlorides accessible in these experiments - one a short-lived upper state, which leads to solvolysis product, and another a long-lived (lower energy) state, which reverts to ground-state reactant.Consistent with this idea, m-methoxybenzyl chloride is shown to quench the photoreactions of benzopenone with benzhydrol without the formation of a significant amount of reactive species.The effects of wavelength on the reactions of p-acetobenzyl chloride are mesured and discussed in terms of the two-triplet concept.
Photochemical Transformations. 26. Sensitized and Unsensitized Photoreactions of Some Benzyl Chlorides in tert-Butyl Alcohol
Cristol, Stanley J.,Bindel, Thomas H.
, p. 951 - 957 (2007/10/02)
Benzyl chloride and a variety of meta- and para-substituted derivatives have been irradiated in tert-butylalcohol at 254 nm or in acetone-tert-butyl alcohol mixtures at 300 nm.Quantum and chemical yields of photosolvolysis products (benzyl tert-butyl ether and/or benzyl alcohol), photohomolysis products (bibenzyl and 4-phenyl-2-methyl-2-butanol), and corresponding products from substituted benzylchlorides have been measured as functions of substrate concentration and medium composition.Sensitized reactions favor bond heterolysis, but direct irradiations favor homolysis, although reactions are not clean in either case.There is no correlation between quantum yields for photosolvolysis and Hammett ? or Brown ?+ constants, and no salt effects of added lithium perchlorate were observed, in either direct or sensitized reactions.
