37854-29-8

Upstream product

• 1792-81-0 cis-1,2-cyclohexane 
• 36967-85-8 benzoyl triflate 
• 931-17-9 1,2-Cyclohexanediol 
• 98-88-4 benzoyl chloride 
• 64548-92-1 N-benzoyl-4-(N,N-dimethylamino)pyridinium chloride 
• 110-86-1 pyridine 
• 65-85-0 benzoic acid 
• 87-66-1 2-hydroxyresorcinol 
• 59694-07-4 (+/-)-trans-2-hydroxycyclohexyl benzoate 

Relevant academic research and scientific papers

Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds

Reversible cleavage of C(sp3)-H bonds can enable racemization or epimerization, offering a valuable tool to edit the stereochemistry of organic compounds. While epimerization reactions operating via cleavage of acidic C(sp3)-H bonds, such as the Cα-H of carbonyl compounds, have been widely used in organic synthesis and enzyme-catalyzed biosynthesis, epimerization of tertiary carbons bearing a nonacidic C(sp3)-H bond is much more challenging with few practical methods available. Herein, we report the first synthetically useful protocol for the epimerization of tertiary carbons via reversible radical cleavage of unactivated C(sp3)-H bonds with hypervalent iodine reagent benziodoxole azide and H2O under mild conditions. These reactions exhibit excellent reactivity and selectivity for unactivated 3° C-H bonds of various cycloalkanes and offer a powerful strategy for editing the stereochemical configurations of carbon scaffolds intractable to conventional methods. Mechanistic study suggests that the unique ability of N3? to serve as a catalytic H atom shuttle is critical to reversibly break and reform 3° C-H bonds with high efficiency and selectivity.

Truncated Cinchona alkaloids as catalysts in enantioselective monobenzoylation of meso-1,2-diols

Readily synthesised quincorine and quincoridine derived chiral diamines efficiently catalyse the asymmetric monobenzoylation of cyclic and acyclic meso-1,2-diols. The Royal Society of Chemistry.

Reduction of diesters of 1,2-diols. Regioselective C-O bond cleavage of the anionic forms

The electrochemical reduction of benzoate diesters of glycols has been studied in acetonitrile and N,N-dimethylformamide as solvents. The reductions occur in two closely spaced one-electron steps, and it was found that the dianion diradicals decompose by one of two routes, depending on the substituents on the ethylene moiety: cleavage of two benzoates to produce alkene or formation of benzil by way of a postulated cyclic intermediate to produce also the dianion of the diol. These correspond to cleavage of the R-OC(O)Ar bonds and the RO-C(O)Ar bonds, respectively. When the radical formed by the former cleavage is a primary or secondary radical, the reaction is too slow to compete with the latter reaction that produces benzil. However, when that radical is either tertiary or benzylic, the former cleavage reaction is fast and no benzil is detected. The dianions of p-cyano- and p-nitrobenzoate esters are rather stable on the voltammetric time scale. However, the addition of lithium ions results in detectable formation of 4,4′-dicyanobenzil from four different p-cyanobenzoate diesters.

Remarkably fast acylation of alcohols with benzoyl chloride promoted by TMEDA

Reaction of alcohols with benzoyl chloride in the presence of TMEDA at - 78°C resulted in very fast acylation to afford the corresponding benzoates in excellent yields.

Asymmetric acylation of meso-diols with benzoyl halide in the presence of a chiral diamine

Nonenzymatic desymmetrization of cis-1,2-cyclohexanediol by the asymmetric acylation with achiral benzoyl chloride in the presence of a chiral diamine derived from (S)-proline took place to give monobenzoate in high optical yield.

Highly efficient catalytic asymmetric acylation of meso-1,2-diols with benzoyl chloride in the presence of a chiral diamine combined with Et3N

Catalytic asymmetric acylation of meso-1,2-diols has been successfully performed by the reaction with benzoyl chloride in the presence of 0.5 mol% of chiral diamine derived from (S)-proline combined with a stoichiometric amount of triethylamine to give th

N-benzoyl-4-(dimethylamino)pyridinium chloride: Isolation and use for the direct benzoylation of alcohols

A simple method for the formation and isolation of N-benzoyl-4- (dimethylamino)pyridinium chloride is described. This reagent can be employed directly for the benzoylation of secondary and tertiary alcohols.

Benzoyl Trifluoromethanesulfonate. A Mild Reagent for the Benzoylation of Sterically Hindered Hydroxyls

Benzoyl trifluoromethanesulfonate (BzOTf) is a highly efficient reagent for the benzoylation of a variety of alcohols under mild conditions.These include hindered secondary and tertiary hydroxyls, phenols, and α-glycols.Sensitive functionality is stable when the reaction is performed in the presence of pyridine.Several unique rearrangements of Lewis acidsensitive compounds were also effected.

STUDIES ON THE SYNTHESIS OF HETEROCYCLIC COMPOUNDS. IX. SEPARATION OF DIASTEREOMERIC DIOL COMPOUNDS

The separation of diastereomeric diols by transformation into the corresponding dioxastannolanes was carried out.The products are solid, stable and easily separable by fractional crystallization.By reaction of acids (or acyl halides) with the stannolanes the corresponding diols (or esters) were obtained in a high degree of purity.The structures of the compounds prepared were assigned on the basis of their analytical, physical and spectral data.

Benzoyl Trifluoromethanesulphonate. A Highly Efficient Benzoylating Agent for Sterically Hindered Hydroxyl Groups

Reactions of benzoyl trifluoromethanesulphonate (BzOTf) with a variety of alcohols, including some with sterically hindered secondary and tertiary hydroxy groups, with phenolic compounds, and with 1,2-diols at low temperatures provide the corresponding benzoates in high yield.