Month: November 2022

Leggetter, B. E. published the artcileInfluence of substituents on the ease and direction of ring opening in the LiAlH₄-AlCl₃ reductive cleavage of substituted 1,3-dioxolanes, Application of 2,2,4-Trimethyl-1,3-dioxolane, the publication is Canadian Journal of Chemistry (1964), 42(5), 990-1004, database is CAplus.

Room temperature hydrogenolysis by LiAlH₄-AlCl₃ of ether solutions of a number of 1,3-dioxolanes was studied. Electron-donor substituents on the C-2 atom of the ring accelerated, while electron-acceptor substituents on C-2 retarded, the reductive ring cleavage. The same effect, but to a lesser extent, was observed when these substituents were attached to the C-4 or C-5 atom of the ring. When electron-donor substituents were attached to C-4, ring cleavage occurred predominantly at the (C-2)-O bond remote from the C-4 position. On the other hand, electron-withdrawing groups attached to C-4 gave predominantly scission of the (C-2)-O bond closer to the C-4 substituted position. In contrast to this marked control over the direction of ring cleavage exhibited by substituents on C-4, those on C-2 generally had little or no effect on the direction of ring opening. A mechanistic interpretation of the results was given.

Canadian Journal of Chemistry published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C6H12O2, Application of 2,2,4-Trimethyl-1,3-dioxolane.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Pritzius, Adrian B. published the artcileAsymmetric Rhodium-Catalyzed Addition of Thiols to Allenes: Synthesis of Branched Allylic Thioethers and Sulfones, Product Details of C38H24F4O4P2, the publication is Angewandte Chemie, International Edition (2015), 54(10), 3121-3125, database is CAplus and MEDLINE.

A highly regio- and enantioselective hydrothiolation of terminal allenes, a reaction which fulfills the criteria of atom economy, is reported. Applying two chiral rhodium catalyst systems, a wide variety of thiols and allenes could be coupled. Oxidation gave access to the corresponding allylic sulfones in essentially enantiomerically pure form. The reaction tolerates a variety of functional groups and labeling experiments gave first insights into the reaction mechanism of this new methodol.

Angewandte Chemie, International Edition published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Product Details of C38H24F4O4P2.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Sontsev, V. M. published the artcileConversion of propylene glycol-acetone mixture into 2,2,4-trimethyl-1,3-dioxolane over Dowex DR-2030 and ZrO₂-SiO₂ acid catalysts, Recommanded Product: 2,2,4-Trimethyl-1,3-dioxolane, the publication is Khimiya, Fizika ta Tekhnologiya Poverkhni (2014), 5(1), 42-46, database is CAplus.

The conversion of propylene glycol-acetone mixtures into cyclic ketal over sulforesin Dowex DR-2030 and acidic ZrO₂-SiO₂ catalysts under steady conditions at 40-100 °C has been studied. It has been shown that 2,2,4-trymethyl-1,3-dioxolane can be obtained with 99-94% yield at 40-50 °C. Conversion of propylene glycol increases from 65 to 75% when providing of the ketalization process with water removing.

Khimiya, Fizika ta Tekhnologiya Poverkhni published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C20H18BrN3, Recommanded Product: 2,2,4-Trimethyl-1,3-dioxolane.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Barker, S. A. published the artcileSpectra of acetals. II. Infrared and Raman spectra of substituted 1,3-dioxolanes, Safety of 2,2,4-Trimethyl-1,3-dioxolane, the publication is Journal of the Chemical Society (1959), 807-13, database is CAplus.

Infrared and Raman spectra have been reported for 9 substituted 1,3-dioxolanes: 2-methyl; 4-methyl; 2,2-dimethyl; cis-2,4-dimethyl; trans-2,4-dimethyl; 2,2,4-trimethyl; 4-hydroxymethyl-2,2-dimethyl; 4-deuterioöxymethyl-2,2-dimethyl; and 4-methoxymethyl-2,2-dimethyl. Infrared and Raman spectra of these compounds were measured. Some 100 bands observed are listed in a table with their assignments made by analogy with the assignments for dioxolane. Internal vibrations of the methyl groups were made by use of the review of Sheppard and Simpson (C.A. 47, 6767d). These assignments are discussed under the following headings: vibrations involving methylene groups; vibrations involving methyl substituents, including bending, rocking, stretching, and deformations of the methyl groups; C-H deformations; vibrations involving a hydroxymethyl substituent; and ring vibrations. The infrared spectra of the 3,4-O-isopropylidene ketals of L-iditol, D-mannitol, and D-sorbitol were measured over the range 650-1500 cm.^-1 Assignments, made by analogy with those for the substituted dioxolanes, are given.

Journal of the Chemical Society published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C6H12O2, Safety of 2,2,4-Trimethyl-1,3-dioxolane.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Barker, S. A. published the artcileSpectra of acetals. I. The infrared and Raman spectra of 1,3-dioxolane, Application In Synthesis of 1193-11-9, the publication is Journal of the Chemical Society (1959), 802-6, database is CAplus.

For eventual application to the interpretation of the spectra of sugar acetals and ketals containing substituted dioxolane ring systems, the Raman and infrared spectra of 1,3-dioxolane have been measured and observed bands have been correlated with vibrational modes giving rise to them. Raman lines were measured within ± 1 cm.^-1 against standard Fe-arc lines, by using a Hilger Raman spectrometer and the exciting line 4358 A. from a Hg lamp. Qual. polarization data were obtained from exposures with Polaroid wrapped around the Raman tube. Infrared absorption spectra were measured on a Grubb-Parsons single beam spectrometer with NaCl and KBr prisms. The C-H stretching frequencies were measured in the 3rd order on a grating spectrometer having a 2500-lines/in. grating. Measurements were carried out in the vapor state, as liquid films, and as CCl₄ solutions The exact geometry of the dioxolane ring is not known but Mills (C.A. 50, 2435i) has suggested that the ring is nearly planar. However, the diffuse nature of the Raman lines and the breadth of the infrared bands indicates a puckered ring. Since the degree of puckering is probably small the symmetry will not deviate far from that of a planar ring. Application of the selection rules to such a planar ring indicates that 27 normal vibrations are expected for 1,3-dioxolane and these expected bands are shown in a table according to symmetry class. Assignments for 25 of these expected bands observed in the Raman or infrared spectra have been made. These bands and their assignments are discussed under the following headings: C-H stretching vibrations; antisym. C-H stretching; vibrations; methylene scissoring, wagging, twisting, and rocking vibrations; and ring vibrations. The 2 fundamentals to which frequencies have not been assigned are the out-of-plane ring frequencies which lie below the limit of the infrared measurements, 420 cm.^-1, and which have not been observed in the Raman effect. Assignment of frequencies has been difficult as the infrared spectrum of 1,3-dioxolane vapor does not exhibit recognizable band shapes and, for the 5 polarized lines expected below 140 cm.^-1 in Raman spectra, only 1 highly polarized line and 1 partially polarized line have been observed as polarized.

Journal of the Chemical Society published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C6H12O2, Application In Synthesis of 1193-11-9.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Tateo, Fernando published the artcileIdentification of 1,3-dioxolanes in coffee-like flavorings, Synthetic Route of 68527-74-2, the publication is Journal of High Resolution Chromatography (1998), 21(12), 658-660, database is CAplus.

Com. available coffee-like flavoring preparations, identifying certain dioxolane structures of particular interest were concerned. The research was carried out by GC/MS, and spectral characterization was performed of the compounds in question, and especially of the acetals and ketals produced from compounds with carbonyl functions and 1,2-propylene glycol. Some determinations by chiral gas chromatog. and by isotope ratio mass spectrometry (IRMS) were useful in improving the anal. characterization of certain dioxolanes.

Journal of High Resolution Chromatography published new progress about 68527-74-2. 68527-74-2 belongs to dioxole, auxiliary class Dioxolane,Benzene,Phenol,Ether, name is 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol, and the molecular formula is C16H20N2, Synthetic Route of 68527-74-2.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Tateo, Fernando published the artcileIdentification of 1,3-dioxolanes in coffee-like flavorings, Recommanded Product: 2,2,4-Trimethyl-1,3-dioxolane, the publication is Journal of High Resolution Chromatography (1998), 21(12), 658-660, database is CAplus.

Com. available coffee-like flavoring preparations, identifying certain dioxolane structures of particular interest were concerned. The research was carried out by GC/MS, and spectral characterization was performed of the compounds in question, and especially of the acetals and ketals produced from compounds with carbonyl functions and 1,2-propylene glycol. Some determinations by chiral gas chromatog. and by isotope ratio mass spectrometry (IRMS) were useful in improving the anal. characterization of certain dioxolanes.

Journal of High Resolution Chromatography published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C10H18O, Recommanded Product: 2,2,4-Trimethyl-1,3-dioxolane.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Barreiro, Elena M. published the artcileAtropisomeric [(diphosphine)Au₂Cl₂] Complexes and their Catalytic Activity Towards Asymmetric Cycloisomerisation of 1,6-Enynes, Category: dioxole, the publication is Chemistry – A European Journal (2015), 21(6), 2686-2690, database is CAplus and MEDLINE.

X-ray crystal structures of two [(diphosphine)Au₂Cl₂] complexes (in which diphosphine = P-Phos and xylyl-P-Phos; P-Phos = [2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine]) were determined and compared to the reported structures of similar atropisomeric gold complexes. Correlations between the Au-Au distances and torsional angles for the biaryl series of ligands (MeOBIPHEP, SEGPhos, and P-Phos; BIPHEP = 2,2′-bis(diphenylphosphino)-1,1′-biphenyl, SEGPhos = [(4,4′-bi-1,3-benzodioxole)-5,5′-diyl]bis[diphenylphosphine]) can be made; these measurements appear to be very dependent upon the phosphorus substituent. Conversely, the same effect was not observed for ligands based on the binaphthyl (BINAP) series. The catalytic activity of these complexes was subsequently assessed in the enantioselective cycloisomerization of 1,6-enynes ArCCCH₂OCH₂CH:CHC₆H₅ (Ar = 4-O₂NC₆H₄, 3-CH₃OC₆H₄, C₆H₅, 4-CH₃C₆H₄) and revealed an over-riding electronic effect: more-electron-rich phosphines promote greater enantioselectivity. The possibility of silver acting as a (co-) catalyst was ruled out in these reactions.

Chemistry – A European Journal published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Category: dioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Fleming, Bruce published the artcileReductive cleavage of acetals and ketals by borane, Quality Control of 1193-11-9, the publication is Canadian Journal of Chemistry (1974), 52(6), 888-93, database is CAplus.

Borane in THF reduced acetals, e.g., PhCH(OMe)2, and ketals, e.g., PhC(OEt)2Me, to ethers in good yield under mild and convenient conditions. Cyclic acetals and ketals were converted to hydroxy ethers. The mechanism resembled that of reduction with LiAlH4-AlCl3.

Canadian Journal of Chemistry published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C6H12O2, Quality Control of 1193-11-9.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Cirkva, V. published the artcileRadical addition reactions of fluorinated species. Part 8. Regioselectivity of radical additions to perfluoroalkylethylenes and quantum chemical calculations. Highly selective two-step synthesis of 4-(perfluoroalkyl)butane-1,2-diols, Computed Properties of 1193-11-9, the publication is Journal of Fluorine Chemistry (2000), 102(1-2), 159-168, database is CAplus.

R_FCH:CH₂ (R_F = C₄F₉, C₆F₁₃, C₈F₁₇) easily added nucleophilic radicals generated from alkanols, oxolane and 2,2-dimethyl-1,3-dioxolane. The additions were initiated photochem. in the presence of Me₂CO or by Bz₂O₂, and were completely regioselective and almost completely chemoselective with preparative yields ≤90%. The resulting 4-(fluoroalkyl)dioxolanes were deprotected by methanolysis in acid media to afford R_FCH₂CH₂CH(OH)CH₂OH, which were converted to the corresponding bis-methacrylates. 2,2,4-Trimethyl-1,3-dioxolane (I) reacted at 2 centers to give an 84:16 regioisomeric mixture of fluoroalkylated dioxolanes with preferential attack of the adduct-radical to the more sterically hindered tertiary C-H bond in I. The complete regioselectivity of the additions to (perfluoroalkyl)ethenes is discussed in relation to the tail effect of the perfluoroalkylated chain, and energies of intermediate adduct-radicals were calculated using PM3 and ab initio quantum-chem. methods.

Journal of Fluorine Chemistry published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C6H12O2, Computed Properties of 1193-11-9.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem