1076-26-2Relevant articles and documents
Irradiation of 1-piperidinomethyl-naphthol-(2) in tetrahydrofuran. 2. Photochemistry of 2-aminomethyl-phenol
Roth,Michel
, (1971)
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Cornforth,Cornforth,Robinson
, (1943)
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Kornblum et al.
, p. 1148,1153 (1963)
Stereoselective synthesis of disubstituted naphthalene-1,2- oxides
Tius,Reddy
, p. 859 - 869 (1994)
Spiroepoxy naphthalenones, obtained from the stereoselective oxidation of 2-hydroxyalkyl-1-naphthols with sodium periodate, were converted to naphthalene-1,2-oxides by reaction with methyllithium followed by Payne rearrangement.
Organocatalytic Asymmetric Dearomatization Reaction for the Synthesis of Axial Chiral Allene-Derived Naphthalenones Bearing Quaternary Stereocenters
Woldegiorgis, Alemayehu Gashaw,Han, Zhao,Lin, Xufeng
, p. 6606 - 6611 (2021)
The highly regio-, diastereo-, and enantioselective dearomatization reaction of 1-substituted 2-naphthols and β,γ-alkynyl-α-imino esters with complete atom economy is disclosed via chiral phosphoric acid catalysis. This protocol provides facile and effici
Oxidation of 2-substituted cycloalkanones with cerium(IV) sulfate tetrahydrate in alcohols and acetic acid
He, Liangyou,Horiuchi, C. Akira
, p. 2515 - 2521 (1999)
The reaction of 2-substituted cycloalkanones with cerium(IV) sulfate tetrahydrate (CS) in alcohols and acetic acid gave the corresponding alkyl esters of oxo acids (80-96%) and oxo acids (78-96%), respectively, by oxidative cleavage of the C(R).C=O bond. In the case of 2-iodocycloalkanones in methanol, the dimethyl ester was obtained in good yield. A treatment of 5α-cholestan-3-one with CS in methanol produced 2-acetal 3-ester of 2,3-seco derivative in good yield. The effects of cerium(IV) and copper(II) salts are also discussed.
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Hill,Short,Higginbottom
, (1938)
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Smith,Horner
, p. 676,678 (1938)
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Site-selective Oxidative Dearomatization of Phenols and Naphthols into ortho-Quinols or Epoxy ortho-Quinols using Oxone as the Source of Dimethyldioxirane
Cabrera-Afonso, María J.,Carre?o, M. Carmen,Urbano, Antonio
supporting information, (2019/08/21)
A novel reactivity of dimethyldioxirane, generated in situ from Oxone and acetone, with substituted phenols and naphthols is reported. This methodology allowed the synthesis of ortho-quinols or epoxy ortho-quinols from a site-selective oxidative dearomatization process, with good yields under very mild conditions. A short total synthesis of natural product lacinilene C methyl ether is also described using this process as the key step. (Figure presented.).
Intermediacy of Ni-Ni Species in sp2 C-O Bond Cleavage of Aryl Esters: Relevance in Catalytic C-Si Bond Formation
Somerville, Rosie J.,Hale, Lillian V. A.,Gómez-Bengoa, Enrique,Burés, Jordi,Martin, Ruben
supporting information, p. 8771 - 8780 (2018/06/25)
Monodentate phosphine ligands are frequently employed in the Ni-catalyzed C-O functionalization of aryl esters. However, the extensive body of preparative work on such reactions contrasts with the lack of information concerning the structure and reactivity of the relevant nickel intermediates. In fact, experimental evidence for a seemingly trivial oxidative addition into the C-O bond of aryl esters with monodentate phosphines and low-valent nickel complexes still remains elusive. Herein, we report a combined experimental and theoretical study on the Ni(0)/PCy3-catalyzed silylation of aryl pivalates with CuF2/CsF additives that reveals the involvement of unorthodox dinickel oxidative addition complexes in C-O bond cleavage and their relevance in C-Si bond formation. We have obtained a mechanistic picture that clarifies the role of the additives and demonstrates that dinickel complexes act as reservoirs of the propagating monomeric nickel complexes by disproportionation. We believe this study will serve as a useful entry point to unravelling the mechanistic underpinnings of other related Ni-catalyzed C-O functionalization reactions employing monodentate phosphines.
