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Search for "dichloro-" in Full Text gives 177 result(s) in Beilstein Journal of Organic Chemistry.

Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis

  • Maddali L. N. Rao,
  • Jalindar B. Talode and
  • Venneti N. Murty

Beilstein J. Org. Chem. 2016, 12, 2065–2076, doi:10.3762/bjoc.12.195

Graphical Abstract
  • functionalized with 5-chloro, 5,7-dichloro, 7-bromo-5-chloro and 5-bromo groups 1.3–1.6 furnished exclusive arylations at C-2 position. In these cases, the corresponding 2-aryl-3-bromobenzofuran products 2.16–2.27 were obtained in high yields (Table 2, entries 16-27). It is to be mentioned that, despite the
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Published 22 Sep 2016

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

  • Jacob R. Hauser,
  • Hester A. Beard,
  • Mary E. Bayana,
  • Katherine E. Jolley,
  • Stuart L. Warriner and
  • Robin S. Bon

Beilstein J. Org. Chem. 2016, 12, 2019–2025, doi:10.3762/bjoc.12.189

Graphical Abstract
  • alternative synthesis of ACBT that avoids the use of cyanide (Scheme 2B) [7]. This route makes use of 4,5-dichloro-1,2,3-dithiazolium chloride (Appel’s salt, 12), and variations of the procedure have enabled the synthesis of different CBT derivatives, some of which on multi-gram scale [6][7][16][17]. However
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Published 13 Sep 2016

Potent triazine-based dehydrocondensing reagents substituted by an amido group

  • Munetaka Kunishima,
  • Daiki Kato,
  • Nobu Kimura,
  • Masanori Kitamura,
  • Kohei Yamada and
  • Kazuhito Hioki

Beilstein J. Org. Chem. 2016, 12, 1897–1903, doi:10.3762/bjoc.12.179

Graphical Abstract
  • substituents (R3 = Me or Ph), and the methyl, phenyl, or hydrogen substituent was placed at R4. Tertiary amide-type compounds III–VI were prepared in one step from the well-known commercially available 2,4-dichloro-6-methoxy-1,3,5-triazine (6) [20] (Scheme 2). In contrast, attempts to prepare the secondary
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Published 24 Aug 2016

Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity

  • Atul A. Dhavan,
  • Rahul D. Kaduskar,
  • Loana Musso,
  • Leonardo Scaglioni,
  • Piera Anna Martino and
  • Sabrina Dallavalle

Beilstein J. Org. Chem. 2016, 12, 1624–1628, doi:10.3762/bjoc.12.159

Graphical Abstract
  • cleavage with cerium ammonium nitrate (CAN) or 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). Thus, 2,3-pyrrolidinedione 3 was obtained by the reaction of ethyl acrylate with p-methoxybenzylamine, followed by treatment with diethyl oxalate (Scheme 1) [12]. On the basis of NMR data, the compound exists as an
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Published 29 Jul 2016

Methylpalladium complexes with pyrimidine-functionalized N-heterocyclic carbene ligands

  • Dirk Meyer and
  • Thomas Strassner

Beilstein J. Org. Chem. 2016, 12, 1557–1565, doi:10.3762/bjoc.12.150

Graphical Abstract
  • reported the synthesis of the imidazolium salts 1–4 and their corresponding silver complexes 5–8. The reaction with dichloro(cyclooctadiene)-palladium(II) [(COD)PdIICl2] allowed for the isolation and characterization of the [((pym)^(NHC-R))PdIICl2]-complexes [34]. For the synthesis of the corresponding
  • could confirm the formation of methyl trifluoroacetate and a ‘methyl free’ Pd(II) complex. This complex showed similar NMR spectra like the bistrifluoroacetate complex 14 (Scheme 3), which was prepared by the reaction of the corresponding dichloro complex [34] with silver trifluoroacetate for comparison
  • palladium dichloro complexes [(pym)^(NHC)PdII(Cl)2] [34]. As the methane activation is carried out in a mixture of trifluoroacetic acid and its anhydride, another potential intermediate could be the [((pym)^(NHC-DIPP))PdII(CH3)(CF3COO)] complex 13. Formation of methyl trifluoroacetate and the
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Published 21 Jul 2016

Indenopyrans – synthesis and photoluminescence properties

  • Andreea Petronela Diac,
  • Ana-Maria Ţepeş,
  • Albert Soran,
  • Ion Grosu,
  • Anamaria Terec,
  • Jean Roncali and
  • Elena Bogdan

Beilstein J. Org. Chem. 2016, 12, 825–834, doi:10.3762/bjoc.12.81

Graphical Abstract
  • obtain photoluminescent compounds with higher performance, the dehydrogenation reaction of enol-lactones 2 and 3 was performed. Adapted from a procedure previously described [38], the oxidation of the isomeric mixture 2'a/3''a and 2'c/3'c, respectively, in the presence of 2,3-dichloro-5,6-dicyano-1,4
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Published 27 Apr 2016

A selective and mild glycosylation method of natural phenolic alcohols

  • Mária Mastihubová and
  • Monika Poláková

Beilstein J. Org. Chem. 2016, 12, 524–530, doi:10.3762/bjoc.12.51

Graphical Abstract
  • performed in the presence of known mild catalysts such as Ag2O [33] (method A), the less frequently used ZnO–ZnCl2 system [34] (method B) and the combination of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with iodine (DDQ–I2) [35] (method C). In addition ZnO–I2 (method D) was successfully applied as a
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Published 15 Mar 2016

A quadruple cascade protocol for the one-pot synthesis of fully-substituted hexahydroisoindolinones from simple substrates

  • Hong-Bo Zhang,
  • Yong-Chun Luo,
  • Xiu-Qin Hu,
  • Yong-Min Liang and
  • Peng-Fei Xu

Beilstein J. Org. Chem. 2016, 12, 253–259, doi:10.3762/bjoc.12.27

Graphical Abstract
  • , entry 11). A heteroaromatic substrate such as thiophene could also be successfully employed to afford rac-3 with medium yield and diastereoselectivity (Table 2, entry 13). 3,4-Dichloro-substituted and 3,5-dimethoxy-substituted substrates produced the desired products in 84% and 55% yield with 20:1 and
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Published 11 Feb 2016

Simple activation by acid of latent Ru-NHC-based metathesis initiators bearing 8-quinolinolate co-ligands

  • Julia Wappel,
  • Roland C. Fischer,
  • Luigi Cavallo,
  • Christian Slugovc and
  • Albert Poater

Beilstein J. Org. Chem. 2016, 12, 154–165, doi:10.3762/bjoc.12.17

Graphical Abstract
  • -heterocyclic carbene bearing precursor complexes M31, HovII or M32 with excess of 5,7-dichloro-8-hydroxyquinoline or 5,7-dibromo-8-hydroxyquinoline in the presence of excess Cs2CO3 as the base (see Scheme 1). The silver-free method [41] resulted in any case in the formation of at least two new products (as
  • outstanding solubility in nonpolar solvents such as n-pentane as well as in nonpolar substrates such as dicylopentadiene (DCPD). Both properties are desired properties for employing the compounds as initiators in solvent free polymerizations. In case of the reaction of M31 with 5,7-dichloro-8-hydroxyquinoline
  • from a series of published N,O-chelating ligands [42]. The minor isolated product 1b featured two 5,7-dichloro-8-quinolinolate ligands and was identified as the OC-6-32 isomer (see Scheme 1). Complexes 1a and 1b account for 90% of the theoretical yield. In case of HovII as the starting complex again
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Published 28 Jan 2016

New metathesis catalyst bearing chromanyl moieties at the N-heterocyclic carbene ligand

  • Agnieszka Hryniewicka,
  • Szymon Suchodolski,
  • Agnieszka Wojtkielewicz,
  • Jacek W. Morzycki and
  • Stanisław Witkowski

Beilstein J. Org. Chem. 2015, 11, 2795–2804, doi:10.3762/bjoc.11.300

Graphical Abstract
  • ) ppm; HRMS (ESI): [M − Cl]+ calcd for C31H43N2O2: 475.3319, found: 475.3308. Some signals in 13C NMR spectrum are doubled (see text “Synthesis of the carbene precursor”). 1,3-Bis[(2,2,5,7,8-pentamethylchroman-6-yl)-2-imidazolidinylidene]dichloro(o-isopropoxyphenylmethylene)ruthenium (9) In a Schlenk
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Published 30 Dec 2015

Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides

  • Hang Ren,
  • Haoyun An,
  • Paul J. Hatala,
  • William C. Stevens Jr,
  • Jingchao Tao and
  • Baicheng He

Beilstein J. Org. Chem. 2015, 11, 2509–2520, doi:10.3762/bjoc.11.272

Graphical Abstract
  • and deprotection of 2,6-dichloropurine 42 was achieved with a saturated solution of ammonia in methanol to furnish 2-chloro-3’-deoxy-3’-fluoroadenosine (16). The 2,6-dichloro-intermediate 42 was coupled with 2-(tributylstannyl)furan catalyzed by bis(triphenylphosphine)palladium(II) chloride in DMF to
  • provide monochloro-intermediate 43 (Method I, entry 16, Table 1). Monochloro-intermediates 44 and 45 were constructed by Suzuki coupling of dichloro-intermediate 42 with 3-thienylboronic acid and phenylboronic acid in toluene (Method II; entries 17 and 18, Table 1), and monochloro-intermediate 46 was
  • -chlorine atom on the intermediate 42 was stable under the Stille and Suzuki reaction conditions and under ammonia deprotection conditions. However, the palladium-catalyzed cross coupling of dichloro-intermediate 42 with organostannane and organoboronic acid reagents resulted in lower yields when compared
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Published 09 Dec 2015

Diversity-oriented synthesis of analogues of the novel macrocyclic peptide FR-225497 through late stage functionalization

  • Jyotiprasad Mukherjee,
  • Suman Sil and
  • Shital Kumar Chattopadhyay

Beilstein J. Org. Chem. 2015, 11, 2487–2492, doi:10.3762/bjoc.11.270

Graphical Abstract
  • (Scheme 2) with ethyl vinyl ketone in the presence of Grubbs’ 1st generation catalyst (G-I) proved to be unsuccessful in our hands under a range of conditions. However, changing to the 2nd-generation catalyst [(1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene
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Published 08 Dec 2015

Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics

  • Kevin Lafaye,
  • Cyril Bosset,
  • Lionel Nicolas,
  • Amandine Guérinot and
  • Janine Cossy

Beilstein J. Org. Chem. 2015, 11, 2223–2241, doi:10.3762/bjoc.11.241

Graphical Abstract
  • the nitrogen atom, steric effects cannot be neglected. Another example of RCM involving alkenes that possess 2-chloropyridines was reported to produce dihydroisoquinoline 57 from 2,6-dichloro-3,4-diallylpyridine (56) [60]. The addition of benzoquinone prevented the isomerization of the double bond and
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Published 18 Nov 2015

2-Hetaryl-1,3-tropolones based on five-membered nitrogen heterocycles: synthesis, structure and properties

  • Yury A. Sayapin,
  • Inna O. Tupaeva,
  • Alexandra A. Kolodina,
  • Eugeny A. Gusakov,
  • Vitaly N. Komissarov,
  • Igor V. Dorogan,
  • Nadezhda I. Makarova,
  • Anatoly V. Metelitsa,
  • Valery V. Tkachev,
  • Sergey M. Aldoshin and
  • Vladimir I. Minkin

Beilstein J. Org. Chem. 2015, 11, 2179–2188, doi:10.3762/bjoc.11.236

Graphical Abstract
  • -trichloro-1,3-tropolone, 2-(benzoxazolyl)-4,5,6,7-tetrachloro-1,3-tropolone, 2-(2-ethoxycarbonyl-3,4-dichloro-6-hydroxyphenyl)benzoxazole, 2-(2-ethoxycarbonyl-6-hydroxy-3,4,5-trichlorophenyl)benzoxazole, 2-(5-chlorobenzothiazolyl)-5,6,7-trichloro-1,3-tropolone and 2-(5-chlorobenzothiazolyl)-4,5,6,7
  • compound is also present a molecule of benzene located in the center of symmetry (0,0,1/2). Molecular structure of 2-(3,3-dimethylindolyl)-5,7-dichloro-6-ethoxy-1,3-tropolone 13. Selected bond lengths (Å): O(1)–C(1) 1.217(2), O(2)–C(3) 1.2563(19), N(1)–C(8) 1.334(2), C(1)–C(2) 1.471(2), C(1)–C(7) 1.508(2
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Published 12 Nov 2015

A new approach to ferrocene derived alkenes via copper-catalyzed olefination

  • Vasily M. Muzalevskiy,
  • Aleksei V. Shastin,
  • Alexandra D. Demidovich,
  • Namiq G. Shikhaliev,
  • Abel M. Magerramov,
  • Victor N. Khrustalev,
  • Rustem D. Rakhimov,
  • Sergey Z. Vatsadze and
  • Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2015, 11, 2072–2078, doi:10.3762/bjoc.11.223

Graphical Abstract
  • at a double bond. Three representative groups of halovinylferrocenes were studied using cyclic voltammetry (Table 1). The first group was formed from three omega-dichloro derivatives 1, 6, and 10. The second one was made from three omega-dibromo products 2, 7, and 11, and the last group consisted of
  • . The values of the respective oxidation potential depend mainly on the amount of the vinyl groups attached to the ferrocene core. There is also the effect of the halogen atom, though to a lesser extent compared to the effect of the amount of vinyl groups. For example, all dichloro and dibromo compounds
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Published 03 Nov 2015

Hexacoordinate Ru-based olefin metathesis catalysts with pH-responsive N-heterocyclic carbene (NHC) and N-donor ligands for ROMP reactions in non-aqueous, aqueous and emulsion conditions

  • Shawna L. Balof,
  • K. Owen Nix,
  • Matthew S. Olliff,
  • Sarah E. Roessler,
  • Arpita Saha,
  • Kevin B. Müller,
  • Ulrich Behrens,
  • Edward J. Valente and
  • Hans-Jörg Schanz

Beilstein J. Org. Chem. 2015, 11, 1960–1972, doi:10.3762/bjoc.11.212

Graphical Abstract
  • ]. Synthesis of (1,3-bis(2’,6’-dimethyl-4’-dimethylaminophenyl)-2-dihydroimidazolidinylidene)dichloro(phenylthiomethylene)(tricyclohexylphosphine)ruthenium(II) (PCy3)Cl2(H2ITap)Ru=CHSPh (9): H2ITap∙HCl (567 mg, 1.41 mmol) and KOt-Bu (180 mg, 1.61 mmol) were heated to 80 °C in heptane (120 mL) for 90 min. After
  • [31P13C] = 14.9 Hz), 30.0 (s), 28.5 (d, 2J[31P13C] = 10.1 Hz), 27.2 (s, PCy3); 31P {1H} NMR (121.4 MHz, C6D6, 20 °C) δ 23.4 (s); Anal. calcd for C44H58Cl2N8Ru: C, 60.68; H, 6.71; N, 12.87; found: C, 60.21; H, 6.77, N, 12.27. Recovery of bis(tricyclohexylphosphine)dichloro(phenylthiomethylene)ruthenium(II
  • ’-dimethyl-4’-dimethylaminophenyl)-2-dihydroimidazolidinylidene)bis(4-dimethylaminopyridine)dichloro(phenylthiomethylene)ruthenium(II) (DMAP)2Cl2(H2ITap)Ru=CHSPh (12): 4-Dimethylaminopyridine (DMAP, 412 mg, 3.38 mmol) was added to a slurry of (PCy3)Cl2(H2ITap)Ru=CHSPh (9, 1.237 g, 1.32 mmol) in tert-butyl
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Published 21 Oct 2015

Nitro-Grela-type complexes containing iodides – robust and selective catalysts for olefin metathesis under challenging conditions

  • Andrzej Tracz,
  • Mateusz Matczak,
  • Katarzyna Urbaniak and
  • Krzysztof Skowerski

Beilstein J. Org. Chem. 2015, 11, 1823–1832, doi:10.3762/bjoc.11.198

Graphical Abstract
  • worse than nG-SIPr. As outlined in Table 2, all tested catalysts were similarly effective in CM of methyl undecenoate 12 with cis-1,4-diacetoxy-2-butene (13), but parent dichloro complexes provided smaller quantities of dimerization product of 12. In CM of 12 with electron deficient methyl acrylate 15
  • , diiodo derivatives were significantly less efficient and provided much more dimer of 12. Apparently nG-I2 and nG-SIPr-I2 can perform noticeably better than parent dichloro complexes only in metathesis of sterically non-demanding substrates. With this knowledge, we decided to test their applicability
  • , which in our initial tests showed the highest efficiency in RCM of 1. In contrast, nG-I2 turned out to be the least sensitive to ethylene. Both dichloro complexes showed similar levels of stability. These results suggest that most stable ruthenium methylidenes were generated from nG-I2. Next, the RCM of
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Published 06 Oct 2015

Consequences of the electronic tuning of latent ruthenium-based olefin metathesis catalysts on their reactivity

  • Karolina Żukowska,
  • Eva Pump,
  • Aleksandra E. Pazio,
  • Krzysztof Woźniak,
  • Luigi Cavallo and
  • Christian Slugovc

Beilstein J. Org. Chem. 2015, 11, 1458–1468, doi:10.3762/bjoc.11.158

Graphical Abstract
  • compound. The studied complexes are very stable at high temperatures up to 140 °C. The placement of an electron-withdrawing functionality translates into an enhanced activity in RCM. While electronically modified precatalysts, which exist predominantly in the trans-dichloro configuration, gave mostly the
  • RCM and a minor amount of the cycloisomerization product, the unmodified congener, which preferentially exists as its cis-dichloro isomer, shows a switched reactivity. The position of the equilibrium between the cis- and the trans-dichloro species was found to be the crucial factor governing the
  • those compounds, a trans–cis isomerization of the chloride ligands was observed in many cases (Scheme 1) [16]. This phenomenon has been widely discussed in literature with multiple reports of superior activity of trans-configured complexes. The general hypothesis is that the trans-dichloro form of the
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Published 20 Aug 2015

Selected synthetic strategies to cyclophanes

  • Sambasivarao Kotha,
  • Mukesh E. Shirbhate and
  • Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

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Published 29 Jul 2015

Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds

  • Gerold Heuger and
  • Richard Göttlich

Beilstein J. Org. Chem. 2015, 11, 1226–1234, doi:10.3762/bjoc.11.136

Graphical Abstract
  • aminohalogenation of cinnamic esters using N,N-dichloro-p-toluenesulfonamide and ZnCl2 or Cu(OTf)2 [18] as catalysts and transferred these conditions to reactions with alkynes [19][20][21] and α,β-unsaturated ketones [19][20][21]. An ionic mechanism via halonium ions was proposed. The amidofluorination of alkenes
  • , 129.3, 136.2, 143.3; MS (EI, 70 eV) m/z (%): 303 (80) [M+], 259 (4) [M − C2H4O+], 241 (11), 214 (14), 196 (12), 155 (31) [C7H7O2S+], 127 (41), 108 (100), 91 (66) [C7H7+], 55 (42) [C3H3O+]; HRMS (EI) m/z: [M+] calcd for C13H18N35ClO3S, 303.06958; found, 303.06931. N-(1,2-Dichloro-2-isobutoxyethyl)-N
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Published 21 Jul 2015

New palladium–oxazoline complexes: Synthesis and evaluation of the optical properties and the catalytic power during the oxidation of textile dyes

  • Rym Hassani,
  • Mahjoub Jabli,
  • Yakdhane Kacem,
  • Jérôme Marrot,
  • Damien Prim and
  • Béchir Ben Hassine

Beilstein J. Org. Chem. 2015, 11, 1175–1186, doi:10.3762/bjoc.11.132

Graphical Abstract
  • , 70.2, 68.0, 31.3, 18.5, 15.9; 31P NMR (MeOD, 75 MHz) δ 36.0 ppm; TOF–MS (ES+) for (C34H31NOPPd): theoretical [M − Cl]+: 602.1199; measured [M − Cl]+: 602.1201; FTIR (KBr pellets, cm−1): 2956.7, 1637.4, 1436.7, 1201.0, 1094.9, 1011.0, 692.3, 513.4. Synthesis of dichloro-[1,2-bis((S)-4-phenyl-4,5
  • methanol, and recrystallized from CHCl3/hexane. Yields of dichloro[bis(4-isopropyl-2-naphthalen-1-yl)oxazoline]palladium(II) (9) and dichloro[bis(4-isopropyl-2-(2-cyanoethyl)oxazoline)]palladium(II) (12) are 85% and 68%, respectively. Complex 9: [α]D −113 ± 28 (c 0.1, MeCN); 1H NMR (CDCl3, 300 MHz) δ 8.49
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Published 15 Jul 2015

Cathodic hydrodimerization of nitroolefins

  • Michael Weßling and
  • Hans J. Schäfer

Beilstein J. Org. Chem. 2015, 11, 1163–1174, doi:10.3762/bjoc.11.131

Graphical Abstract
  • is the pyrrole derivative 22, in the air its light colour deepens quickly to brown. The electrolyses proceed uniformly. The current reaches after a short induction period (1–3 min) depending on the substrate a maximal current of 250–450 mA, which then decreases exponentially to zero. The dichloro
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Published 14 Jul 2015

Advances in the synthesis of functionalised pyrrolotetrathiafulvalenes

  • Luke J. O’Driscoll,
  • Sissel S. Andersen,
  • Marta V. Solano,
  • Dan Bendixen,
  • Morten Jensen,
  • Troels Duedal,
  • Jess Lycoops,
  • Cornelia van der Pol,
  • Rebecca E. Sørensen,
  • Karina R. Larsen,
  • Kenneth Myntman,
  • Christian Henriksen,
  • Stinne W. Hansen and
  • Jan O. Jeppesen

Beilstein J. Org. Chem. 2015, 11, 1112–1122, doi:10.3762/bjoc.11.125

Graphical Abstract
  • the cyclised product 14. Crude material of sufficient purity for the following step can be isolated by precipitation (see the Experimental section in the Supporting Information File 1). Transchalcogenation of crude 14 affords 15 and aromatisation of crude 15 using 2,3-dichloro-5,6-dicyano-1,4
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Published 03 Jul 2015

Bis(vinylenedithio)tetrathiafulvalene analogues of BEDT-TTF

  • Erdal Ertas,
  • İlknur Demirtas and
  • Turan Ozturk

Beilstein J. Org. Chem. 2015, 11, 403–415, doi:10.3762/bjoc.11.46

Graphical Abstract
  • of 52 was prepared with the acceptor 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) 53 (1:1) in dichloromethane at room temperature to investigate the optical constant and optical band gap of the complex (Scheme 8) [56]. A solution of the salt was evaporated on a quartz substrate until ≈110 nm
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Published 27 Mar 2015

Electrochemical oxidation of cholesterol

  • Jacek W. Morzycki and
  • Andrzej Sobkowiak

Beilstein J. Org. Chem. 2015, 11, 392–402, doi:10.3762/bjoc.11.45

Graphical Abstract
  • , which were anodically oxidized to chlorine. The electrophilic addition of chlorine to the double bond of the investigated compounds cholesteryl acetate (1a), cholesteryl benzoate (1b), 3β-chloro-5-cholestene (1c), and 5-cholestene (1d), gave the corresponding 5α,6β-dichloro steroids in good yields (70
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Published 25 Mar 2015
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