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Molecules, Volume 6, Issue 11 (November 2001), Pages 845-926

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Research

Open AccessArticle Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?
Molecules 2001, 6(11), 845-851; doi:10.3390/61100845
Received: 3 September 2001 / Revised: 15 October 2001 / Accepted: 16 October 2001 / Published: 31 October 2001
Cited by 13 | PDF Full-text (81 KB) | HTML Full-text | XML Full-text
Abstract
We report that a subtle balance of carbanion reactivity, leaving group activation, and pKa of the catalyst is required for efficient self-condensation of thiomalonates to thioacetoacetates in up to 71% yield under “biomimetic” conditions originally proposed by Kobuke and Yoshida (Tetrahedron [...] Read more.
We report that a subtle balance of carbanion reactivity, leaving group activation, and pKa of the catalyst is required for efficient self-condensation of thiomalonates to thioacetoacetates in up to 71% yield under “biomimetic” conditions originally proposed by Kobuke and Yoshida (Tetrahedron Lett. 1978, 19, 367). Full article
Open AccessArticle Amine and Titanium (IV) Chloride, Boron (III) Chloride or Zirconium (IV) Chloride-Promoted Baylis-Hillman Reactions
Molecules 2001, 6(11), 852-868; doi:10.3390/61100852
Received: 27 April 2001 / Revised: 11 October 2001 / Accepted: 18 October 2001 / Published: 31 October 2001
Cited by 11 | PDF Full-text (95 KB) | HTML Full-text | XML Full-text
Abstract
The Baylis-Hillman reactions of various aryl aldehydes with methyl vinyl ketone at temperatures below -20oC using Lewis acids such as titanium (IV) chloride, boron (III) chloride or zirconium (IV) chloride in the presence of a catalytic amount of selected amines used as [...] Read more.
The Baylis-Hillman reactions of various aryl aldehydes with methyl vinyl ketone at temperatures below -20oC using Lewis acids such as titanium (IV) chloride, boron (III) chloride or zirconium (IV) chloride in the presence of a catalytic amount of selected amines used as a Lewis bases afford the chlorinated compounds 1 as the major product in very high yields. Acrylonitrile can also undergo the same reaction to give the corresponding chlorinated product in moderate yield. A plausible reaction mechanism is proposed. However, if the reaction was carried out at room temperature (ca. 20oC), then the Z-configuration of the elimination product 3, derived from 1, was formed as the major product. Full article
Open AccessArticle One-Pot Procedures for Preparing (Dichloroiodo)arenes from Arenes and Diiodine, with Chromium(VI) Oxide as the Oxidant
Molecules 2001, 6(11), 869-874; doi:10.3390/61100869
Received: 27 September 2001 / Revised: 11 October 2001 / Accepted: 12 October 2001 / Published: 31 October 2001
Cited by 4 | PDF Full-text (33 KB) | HTML Full-text | XML Full-text
Abstract
Ten representative (dichloroiodo)arenes, ArICl2, were prepared from the corresponding arenes and diiodine in variable anhydrous mixtures, ArH/I2/CrO3/AcOH/Ac2O/conc. H2SO4, followed by the addition of conc. hydrochloric acid, used as the source [...] Read more.
Ten representative (dichloroiodo)arenes, ArICl2, were prepared from the corresponding arenes and diiodine in variable anhydrous mixtures, ArH/I2/CrO3/AcOH/Ac2O/conc. H2SO4, followed by the addition of conc. hydrochloric acid, used as the source of chlorine; ArICl2 are useful in organic synthesis as mild and selective chlorinating and/or oxidizing agents. Full article
Open AccessArticle One-Pot Preparations of Diaryliodonium Bromides from Iodoarenes and Arenes, with Sodium Perborate as the Oxidant
Molecules 2001, 6(11), 875-880; doi:10.3390/61100875
Received: 27 September 2001 / Revised: 11 October 2001 / Accepted: 12 October 2001 / Published: 31 October 2001
Cited by 8 | PDF Full-text (35 KB) | HTML Full-text | XML Full-text
Abstract
This paper reports a one-pot synthesis of the title bromides from both activated and deactivated iodoarenes which are first oxidized with anhydrous NaBO3·H2O/Ac2O/conc.H2SO4 liquid mixtures, then coupled in situ with benzene and activated [...] Read more.
This paper reports a one-pot synthesis of the title bromides from both activated and deactivated iodoarenes which are first oxidized with anhydrous NaBO3·H2O/Ac2O/conc.H2SO4 liquid mixtures, then coupled in situ with benzene and activated arenes and, finally, precipitated out with a KBr solution; this method is easy, cheap, safe and fairly effective. Full article
Open AccessArticle Syntheses of (Diacetoxyiodo)arenes or Iodylarenes from Iodoarenes, with Sodium Periodate as the Oxidant
Molecules 2001, 6(11), 881-891; doi:10.3390/61100881
Received: 27 September 2001 / Revised: 11 October 2001 / Accepted: 12 October 2001 / Published: 31 October 2001
Cited by 34 | PDF Full-text (103 KB) | HTML Full-text | XML Full-text
Abstract
- Easy, safe, and effective novel methods for preparing either (diacetoxyiodo)-arenes, ArI(OAc)2, or iodylarenes, ArIO2, from the corresponding iodoarenes, ArI, using sodium periodate as the oxidant are presented in this paper. In order to obtain 2- and 4-iodylbenzoic [...] Read more.
- Easy, safe, and effective novel methods for preparing either (diacetoxyiodo)-arenes, ArI(OAc)2, or iodylarenes, ArIO2, from the corresponding iodoarenes, ArI, using sodium periodate as the oxidant are presented in this paper. In order to obtain 2- and 4-iodylbenzoic acids, the respective sodium salts of 2- and 4-iodobenzoic acids should be used as the starting substrates, because mixtures containing the corresponding iodosyl derivatives as the main products along with the intended iodyl compounds are produced from the free parent acids. Full article
Open AccessArticle Captodative Formyl Enamines in a New Synthesis of Tertiary α-Amino Esters
Molecules 2001, 6(11), 892-899; doi:10.3390/61100892
Received: 26 February 2001 / Revised: 15 October 2001 / Accepted: 18 October 2001 / Published: 31 October 2001
Cited by 6 | PDF Full-text (119 KB) | HTML Full-text | XML Full-text
Abstract A strategy to create the –CH(NR2)CO- moiety from captodative formyl enamines was successfully applied to the synthesis of tertiary α-amino esters. Full article
Open AccessArticle Efficient, Solvent-Free Oxidation of Organic Compounds with Potassium Dichromate in the Presence of Lewis Acids
Molecules 2001, 6(11), 900-908; doi:10.3390/61100900
Received: 9 August 2001 / Revised: 25 September 2001 / Accepted: 22 October 2001 / Published: 31 October 2001
Cited by 8 | PDF Full-text (81 KB) | HTML Full-text | XML Full-text
Abstract
The synthetic utility of potassium dichromate in the presence of Lewis acids under solid phase conditions is described. This reagent efficiently oxidizes alcohols, acyloins, oximes and semicarbazones to their corresponding carbonyl compounds, while trimethylsilyl and tetrahydropyranyl ethers, ethylene acetals and ketals undergo [...] Read more.
The synthetic utility of potassium dichromate in the presence of Lewis acids under solid phase conditions is described. This reagent efficiently oxidizes alcohols, acyloins, oximes and semicarbazones to their corresponding carbonyl compounds, while trimethylsilyl and tetrahydropyranyl ethers, ethylene acetals and ketals undergo oxidative deprotection to produce carbonyl compounds efficiently. Full article
Open AccessArticle Synthesis and Crystal Structure Determination of a Nickel(II) Complex of an Acyclic Pentadentate (N5) Mono Schiff Base Ligand
Molecules 2001, 6(11), 909-914; doi:10.3390/61100909
Received: 19 June 2001 / Revised: 24 September 2001 / Accepted: 22 October 2001 / Published: 31 October 2001
Cited by 8 | PDF Full-text (172 KB) | HTML Full-text | XML Full-text
Abstract
The asymmetrical tripodal tetraamine ligand N[(CH2)3NH2]2[(CH2)2NH2] (ppe) was condensed with 2-acetylpyridine in the presence of nickel(II) ion. In ethanolwater solution the reaction stops after the first stage of [...] Read more.
The asymmetrical tripodal tetraamine ligand N[(CH2)3NH2]2[(CH2)2NH2] (ppe) was condensed with 2-acetylpyridine in the presence of nickel(II) ion. In ethanolwater solution the reaction stops after the first stage of condensation, and a new nickel(II) complex of an acyclic pentadentate (N5) mono Schiff base ligand was obtained. X-ray structure analysis of the resulting complex, [Ni(ppe-py)(H2O)](ClO4)2, indicates that condensation with 2-acetylpyridine is at the propylene chain of ppe. The geometry around the nickel ion is distorted octahedral in which the sixth co-ordination group is a solvent molecule. Full article
Open AccessArticle A New Effective Algorithm for the Unambiguous Identification of the Stereochemical Characteristics of Compounds During Their Registration in Databases
Molecules 2001, 6(11), 915-926; doi:10.3390/61100915
Received: 15 July 2001 / Accepted: 24 October 2001 / Published: 31 October 2001
Cited by 2 | PDF Full-text (59 KB) | HTML Full-text | XML Full-text
Abstract
A new effective algorithm for handling of geometry at chiral centers for the processing of stereochemical structures during their unambiguous registration in databases was designed, programmed and implemented. The chemical and mathematical reasoning behind the algorithm are discussed in detail. Its advantages- [...] Read more.
A new effective algorithm for handling of geometry at chiral centers for the processing of stereochemical structures during their unambiguous registration in databases was designed, programmed and implemented. The chemical and mathematical reasoning behind the algorithm are discussed in detail. Its advantages- in comparison to the methods used so far - are illustrated for the manual as well as for the computerassisted assignment of stereodescriptors based on the CIP ranking procedure. Full article

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