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Propargyl Alcohols (propargyl + alcohol)

Distribution by Scientific Domains
Chemistry100%
Distribution within Chemistry
Organic Chemistry66%
General & Introductory Chemistry27%

Selected Abstracts

Ruthenium-Catalyzed Allenyl Carbamate Formation from Propargyl Alcohols and Isocyanates

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 5 2008
Edgar Haak
Abstract Ruthenium complexes of redox-coupled cyclopentadienone ligands catalyze the formation of allenyl carbamates from propargyl alcohols and isocyanates. This efficient and atom-economical process represents the first catalytic access to allenyl carbamates, compounds of high synthetic potential. The reaction needs an acidic co-catalyst and can be performed at room temperature. In addition, new (cyclopentadienone)iron and -ruthenium complexes were synthesized, and mechanistic aspects regarding catalytic transformations of propargyl systems with ruthenium catalysts are obtained. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [source]

ChemInform Abstract: Generation of Nucleophilic Chromium Acetylides from gem-Trichloroalkanes and Chromium Chloride: Synthesis of Propargyl Alcohols.

CHEMINFORM, Issue 33 2010
Dhurke Kashinath
No abstract is available for this article. [source]

ChemInform Abstract: Synthesis of Functionalized ,-Lactones via Silylcarbocyclization/Desilylation Reactions of Propargyl Alcohols.

CHEMINFORM, Issue 19 2010
Laura Antonella Aronica
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Platinum-Catalyzed Multi-Step Reaction of Propargyl Alcohols with N-Heteroaromatics.

CHEMINFORM, Issue 17 2010
Sivakolundu Bhuvaneswari
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: An Extremely Facile Synthesis of Furans, Pyrroles, and Thiophenes by the Dehydrative Cyclization of Propargyl Alcohols.

CHEMINFORM, Issue 11 2010
Aaron Aponick
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: InBr3 -Catalyzed Annulations of Cyclic 1,3-Diketones with Aryl Propargyl Alcohols: A Novel Synthesis of 2,4-Diaryldihydropyrans.

CHEMINFORM, Issue 42 2009
J. S. Yadav
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Preparation of Disubstituted Phenyl Propargyl Alcohols, Their Use in Oxathiolene Oxide Synthesis, and Evaluation of the Oxathiolene Oxide Products as Anticarcinogenic Enzyme Inducers.

CHEMINFORM, Issue 35 2009
Maben Ying
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: An Efficient Oxidation of Element-Containing Propargyl Alcohols and Acetylenic ,-Diols by 2-Iodoxybenzoic Acid (IBX).

CHEMINFORM, Issue 13 2009
Irina A. Novokshonova
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

Stereoselective Formation of ,-Alkylidene Cyclic Carbonates via Carboxylative Cyclization of Propargyl Alcohols in Supercritical Carbon Dioxide.

CHEMINFORM, Issue 21 2007
Yoshihito Kayaki
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]

ChemInform Abstract: Atom Economy: Aldol-Type Products by Vanadium-Catalyzed Additions of Propargyl Alcohols and Aldehydes.

CHEMINFORM, Issue 25 2001
Barry M. Trost
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

Convergent Synthesis of Both Enantiomers of 4-Hydroxypent-2-ynoic Acid Diphenylamide for a Thrombin Receptor Antagonist Sch,530348 and Himbacine Analogues

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 14-15 2009
Alex Zaks
Abstract Sch,530348 and many himbacine analogues were prepared by using 4-hydroxypent-2-ynoic acid diphenylamide as the only chiral material. We developed deracemization methods to prepare both enantiomers of this propargyl alcohol. These methods involved a resolution followed by inversion. The objective for the resolution step was to obtain the desired enantiomer as an ester, and undesired enantiomer as an alcohol. With (R)-selective lipase, this was achieved by transesterifcation for (R)-alcohol, and ester hydrolysis for (S)-alcohol. The undesired enantiomer was inverted through the corresponding tosylate to yield the desired enantiomer as the ester. Deprotection of the ester gave enantiopure alcohol as the product. These methods not only overcame the 50% yield limit in resolution, but also eliminated the need to remove the undesired enantiomer. [source]

Chiral Ruthenium,Allenylidene Complexes That Bear a Fullerene Cyclopentadienyl Ligand: Synthesis, Characterization, and Remote Chirality Transfer

CHEMISTRY - AN ASIAN JOURNAL, Issue 3 2007
Yu-Wu Zhong Dr.
Abstract Ruthenium complexes that bear both a fullerene and an allenylidene ligand, [Ru(C60Me5)((R)-prophos)=CCCR1R2]PF6 (prophos=1,2-bis(diphenylphosphanyl)propane), were prepared by the reaction of [Ru(C60Me5)Cl((R)-prophos)] and a propargyl alcohol in better than 90,% yields, and characterized by 1H, 13C, and 31P,NMR, IR, and UV/Vis/NIR spectroscopy and MS. Cyclic voltammograms of these complexes showed one reversible or irreversible reduction wave due to the allenylidene part, and two reversible reduction waves due to the fullerene core. Nucleophilic addition of RMgBr or RLi proceeded regioselectively at the distal carbon atom of the allenylidene array. The reaction took place with a 60:40,95:5 level of diastereoselectivity with respect to the original chirality in the (R)-prophos ligand, which is located six atoms away from the electrophilic carbon center. [source]

Ruthenium-Catalyzed Allenyl Carbamate Formation from Propargyl Alcohols and Isocyanates

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 5 2008
Edgar Haak
Abstract Ruthenium complexes of redox-coupled cyclopentadienone ligands catalyze the formation of allenyl carbamates from propargyl alcohols and isocyanates. This efficient and atom-economical process represents the first catalytic access to allenyl carbamates, compounds of high synthetic potential. The reaction needs an acidic co-catalyst and can be performed at room temperature. In addition, new (cyclopentadienone)iron and -ruthenium complexes were synthesized, and mechanistic aspects regarding catalytic transformations of propargyl systems with ruthenium catalysts are obtained. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [source]

Oligonucleotide Analogues with Integrated Bases and Backbone.

HELVETICA CHIMICA ACTA, Issue 4 2007
Part 1
Abstract The self-complementary tetrameric propargyl triols 8, 14, 18, and 21 were synthesized to investigate the duplex formation of self-complementary, ethynylene-linked UUAA, AAUU, UAUA, and AUAU analogues with integrated bases and backbone (ONIBs). The linear synthesis is based on repetitive Sonogashira couplings and C -desilylations (34,72% yield), starting from the monomeric propargyl alcohols 9 and 15 and the iodinated nucleosides 3, 7, 11, and 13. Strongly persistent intramolecular H-bonds from the propargylic OH groups to N(3) of the adenosine units prevent the gg -type orientation of the ethynyl groups at C(5,). As such, an orientation is required for the formation of cyclic duplexes, this H-bond prevents the formation of duplexes connected by all four base pairs. However, the central units of the UAUA and AAUU analogues 18 and 14 associate in CDCl3/(D6)DMSO 10,:,1 to form a cyclic duplex characterized by reverse Hoogsteen base pairing. The UUAA tetramer 8 forms a cyclic UU homoduplex, while the AUAU tetramer 21 forms only linear associates. Duplex formation of the O -silylated UUAA and AAUU tetramers is no longer prevented. The self-complementary UUAA tetramer 22 forms Watson,Crick - and Hoogsteen -type base-paired cyclic duplexes more readily than the sequence-isomeric AAUU tetramer 23, further illustrating the sequence selectivity of duplex formation. [source]

Reactions of Chlorosulfanyl Derivatives of Cyclobutanones with Different Nucleophiles

HELVETICA CHIMICA ACTA, Issue 5 2006
Agnieszka Majchrzak
Abstract The reactions of 3-chloro-3-(chlorosulfanyl)-2,2,4,4-tetramethylcyclobutan-1-one (2) with N, O, S, and P nucleophiles occur by substitution of Cl at the S-atom. Whereas, in the cases of secondary amines, alkanols, phenols, thiols, thiophenols, and di- and trialkyl phosphates, the initially formed substitution products were obtained, the corresponding products with allyl and propargyl alcohols undergo a [2,3]-sigmatropic rearrangement to give allyl and allenyl sulfoxides, respectively. Analogous substitution reactions were observed when 3-chloro-3-(chlorodisulfanyl)-2,2,4,4-tetramethylcyclobutan-1-one (3) was treated with N, O, and S nucleophiles. The reaction of 3 with Et3P led to an unexpected product via cleavage of the SS bond (cf. Scheme,13). In the reactions of 2 with primary amines and H2O, the substitution products react further via elimination of HCl to yield the corresponding thiocarbonyl S -imides and the thiocarbonyl S -oxide, respectively. Whereas the latter could be isolated, the former were not stable but could be intercepted by MeOH (Scheme,4) or adamantanethione (Scheme,5). The structures of some of the substitution products were established by X-ray crystallography. [source]

A highly efficient synthesis of (Z)-1-aryl-2-silyl-1- stannylethenes and their conversion to (E)-2- arylethenyl-, (Z)-2-(2-pyridyl)ethenyl- and allenyl-silanes

APPLIED ORGANOMETALLIC CHEMISTRY, Issue 3 2007
Takanori Endo
Abstract A Pd(dba)2,P(OEt)3 combination allowed the silastannation of arylacetylenes, 1-hexyne or propargyl alcohols with tributyl(trimethylsilyl)stannane to take place at room temperature, producing (Z)-2-silyl-1-stannyl-1-substituted ethenes in high yields. Novel silyl(stannyl)ethenes were fully characterized by 1H-, 13C-, 29Si- and 119Sn-NMR as well as infrared and mass analyses. Treatment of a series of (Z)-1-aryl-2-silyl-1-stannylethenes and (Z)-1-(3-pyridyl)-2-silyl-1-stannylethene with hydrochloric acid or hydroiodic acid in the presence of tetraethylammonium chloride (TEACl) or tetrabutylammonium iodide (TBAI) led to the exclusive formation of (E)-trimethyl(2-arylethenyl)silanes with high stereoselectivity. A similar reaction of (Z)-1-(2-anisyl)-2-silyl-1-stannylethene also produced E -type trimethyl[2-(2-anisyl)ethenyl]silane, while (Z)-trimethyl [2-(2-pyridyl)ethenyl]silane was produced exclusively from (Z)-1-(2-pyridyl)-2-silyl-1-stannylethene. Protodestannylation of (Z)-1-[hydroxy(phenyl)methyl]-2-silyl-1-stannylethene with trifluoroacetic acid took place via the ,-elimination of hydroxystannane, providing trimethyl(3-phenylpropa-1,2-dienyl)silane quite easily. The destannylation products were also fully characterized. Copyright © 2007 John Wiley & Sons, Ltd. [source]

Synthesis of ,-Methoxyacrylate Natural Products Based on Box-PdII -Catalyzed Intermolecular Methoxycarbonylation of Alkynoles

CHEMISTRY - AN ASIAN JOURNAL, Issue 10 2010
Satoshi Motodate
Abstract Bis(oxazoline)-palladium(II) catalyzed carbonylation of homopropargyl alcohols afforded acyclic methoxyacrylate 2 and 6-membered lactone 3,a,k in good combined yield. In the case of propargyl alcohols, 5-membered lactones 3,p, 3,q, 16 were obtained in moderate yields. The one-pot synthesis of kawa lactones 3,a, 3,r, 3,s and formal synthesis of dihydroxycystothiazole,A and dihydroxycystothiazole,C are presented. To elucidate the stereochemistry of (+)-annularin G and (,)-annularin H, the first asymmetric syntheses of these natural products were achieved. [source]

Enantioselective Addition of Phenylacetylene to Ketones Catalyzed by Titanium(IV) Complexes of N -Sulfonylated , -Amino Alcohols

CHINESE JOURNAL OF CHEMISTRY, Issue 2 2006
Shao-Hua Wang
Abstract The easily prepared and recoverable chiral N -sulfonylated , -amino alcohol 2 in combination with Ti(OPr- i)4was found to be an effective chiral catalyst for the enantioselective addition of alkynylzinc to ketones, which gave the useful products, i.e. chiral tertiary propargyl alcohols, with the ee up to 92%. [source]