Pyridinium chlorochromate: an improved method for its synthesis and use of anhydrous acetic acid as catalyst for oxidation reactions

Agarwal, S.; Tiwari, H. P.; Sharma, J. P.

doi:10.1016/s0040-4020(01)86776-4

Cited by 37 publications

(11 citation statements)

References 9 publications

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“…Pyridinium chlorochromate (PCC) has been used extensively for the oxidation of primary alcohols to aldehydes. [44–46] Initially following the procedure described by Sanders and co-workers,[47] treating alcohol 14 with PCC (1.5 equiv.) gave aldehyde 16 in poor yield (6%), again, after chromatographic purification (Table 1, entry 4).…”

Section: Resultsmentioning

confidence: 99%

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

Hickey

Ashton

Boer

et al. 2018

European Journal of Medicinal Chemistry

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The design, synthesis and evaluation of a small series of potent amphiphilic norbornane antibacterial agents has been performed (compound 10 MIC = 0.25 μg/mL against MRSA). Molecular modelling indicates rapid aggregation of this class of antibacterial agent prior to membrane association and insertion. Two fluorescent analogues (compound 29 with 4-amino-naphthalimide and 34 with 4-nitrobenz-2-oxa-1,3-diazole fluorophores) with good activity (MIC = 0.5 μg/mL against MRSA) were also constructed and confocal microscopy studies indicate that the primary site of interaction for this family of compounds is the bacterial membrane.

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Section: Resultsmentioning

confidence: 99%

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

Hickey

Ashton

Boer

et al. 2018

European Journal of Medicinal Chemistry

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“…The isoprenoid dicarbonyl compounds 1 and 2 were synthesized according to the method outlined in Scheme 1 for compound 2, based on procedures in the literature for analogous compounds (step a, [33] b, [34] c, [35] d, [36] e, [36] f, [37] g, [38] , and h [39] ) and described in detail below, beginning with the preparation of 16. Compound 3 was prepared from (±)-camphorsulfonic acid by formation of the sulfonyl chloride, conversion to the sulfonamide, and oxidation to the camphorquinone by analogy to a literature procedure [40] for camphorquinonesulfonamides of α-amino acids, as described in detail below.…”

Section: Synthetic Strategymentioning

confidence: 99%

Inactivation of Protein Farnesyltransferase by Active-Site-Targeted Dicarbonyl Compounds

Okolotowicz

Lee

Hartman

et al. 2001

Arch. Pharm. Pharm. Med. Chem.

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“…Dimethyl sulfoxide (DMSO) activated by various electrophiles is employed in the well-known Swern, − Pfitzner–Moffat, Corey–Kim, , and Parikh–Doering oxidations; however, these reactions may include expensive reagents, stringent reaction conditions, or undesirable byproducts. Transition-metal-containing compounds have also been used, especially high-valent Cr compounds such as the Collins reagent (CrO 3 ·2pyr), pyridinium chlorochromate (PCC), , pyridinium dichromate (PDC), and CrO 3 /H 2 SO 4 (Jones oxidation), but the acute toxicity of Cr poses significant health and environmental risks.…”

Section: Introductionmentioning

confidence: 99%

Reversible PCET and Ambient Catalytic Oxidative Alcohol Dehydrogenation by {V=O} Perfluoropinacolate Complexes

et al. 2020

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A new air-stable catalyst for the oxidative dehydrogenation of benzylic alcohols under ambient conditions has been developed. The synthesis and characterization of this compound and the related monomeric and dimeric V(IV)- and V(V)-pinF (pinF = perfluoropinacolate) complexes are reported herein. Monomeric V(IV) complex (Me4N)2[V(O)(pinF)2] (1) and dimeric (μ-O)2-bridged V(V) complex (Me4N)2[V2(O)2(μ-O)2(pinF)2] (3a) are prepared in water under ambient conditions. Monomeric V(V) complex (Me4N)[V(O)(pinF)2] (2) may be generated via chemical oxidation of 1 under an inert atmosphere, but dimerizes to 3a upon exposure to air. Complexes 1 and 2 display a perfectly reversible VIV/V couple at 20 mV (vs Ag/AgNO3), whereas a quasi-reversible VIV/V couple at −865 mV is found for 3a. Stoichiometric reactions of 3a with both fluorenol and TEMPOH result in the formation of (Me4N)2[V2(O)2(μ-OH)2(pinF)2] (4a), which contains two V(IV) centers that display antiferromagnetic coupling. In order to structurally characterize the dinuclear anion of 4a, {K(18C6)}+ countercations were employed, which formed stabilizing K···O interactions between the counterion and each terminal oxo moiety and H-bonding between the oxygen atoms of the crown ether and μ-OH bridges of the dimer, resulting in {K(18C6)}2[V2(O)2(μ-OH)2(pinF)2] (4b). The formal storage of H2 in 4a is reversible and proton-coupled electron transfer (PCET) from crystals of 4a regenerates 3a upon exposure to air over the course of several days. Furthermore, the reaction of 3a (2%) under ambient conditions with excess fluorenol, cinnamyl alcohol, or benzyl alcohol resulted in the selective formation of fluorenone (82% conversion), cinnamaldehyde (40%), or benzaldehyde (7%), respectively, reproducing oxidative alcohol dehydrogenation (OAD) chemistry known for VO x surfaces and demonstrating, in air, the thermodynamically challenging selective oxidation of alcohols to aldehydes/ketones.

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Pyridinium chlorochromate: an improved method for its synthesis and use of anhydrous acetic acid as catalyst for oxidation reactions

Cited by 37 publications

References 9 publications

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

Inactivation of Protein Farnesyltransferase by Active-Site-Targeted Dicarbonyl Compounds

Reversible PCET and Ambient Catalytic Oxidative Alcohol Dehydrogenation by {V=O} Perfluoropinacolate Complexes

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