Beilstein J. Org. Chem.2021,17, 581–588, doi:10.3762/bjoc.17.52
to its toxicity, the oxidation rate affording trans-diols was very slow in comparison to that for cis-diols. Using an even longer reaction time and stoichiometric amount of the reagent, diol 5 was not oxidized to the corresponding dicarbonyl compound 8. However, using NaOCl·5H2O as an oxidant [31
) NaBH4, EtOH/CH2Cl2 1:1, 2 h, rt, then acetone, H2O, NaIO4, overnight, rt, 99%; ii) Ac2O, p-TsOH (1 mol %), MW (800 W), 6 min, 52% for 3 and 33% for 4; iii) Ac2O, DMAP, Et3N, CH2Cl2, overnight, rt, 93%.
Oxidation of diols 5 and 6 with NaOCl·5H2O.
Enzymatic hydroxylation.
Supporting Information
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Graphical Abstract
Figure 1:
A) Tetracyclic core of steroids and possible sites of bond cleavages for secosteroids. B)The first ...
Beilstein J. Org. Chem.2019,15, 1786–1794, doi:10.3762/bjoc.15.172
l’Ecole Normale, 34296 Montpellier, Cedex 5, France 10.3762/bjoc.15.172 Abstract Aimed at eliminating or at least significantly reducing the use of solvents, sodium hypochlorite pentahydrate crystals (NaOCl·5H2O) in the presence of a catalytic amount of a nitrosyl radical (TEMPO or AZADO) have been
a mechanochemical process.
Keywords: AZADO; Ertalyte®; green chemistry; mechanochemistry; NaOCl·5H2O; selective oxidation; TEMPO; Introduction
The conversion of primary and secondary alcohols to the corresponding carbonyl compounds (aldehydes and ketones, respectively) is of such importance in
. In particular, in this study, we used sodium hypochlorite pentahydrate (NaOCl·5H2O) in the presence of a catalytic amount of a nitrosyl radical (TEMPO or AZADO) to induce mechanochemical oxidation reactions on suitably selected primary and secondary alcohols. Performed in a high-energy ball mill and
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Graphical Abstract
Scheme 1:
Oxidation of 3-pheny-1-propanol (1a) with N-chlorosuccinimide (NCS) in the presence of (2,2,6,6-tet...