55110-61-7Relevant academic research and scientific papers
Cyclic eneyne compound and synthesis method thereof
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, (2017/10/05)
The invention relates to a cyclic eneyne compound and a preparation method thereof. The chemical formula is described in the description, wherein substituent R is any one of phenyl or p-methylphenyl or isohexyl or n-heptyl, ring is a five-membered ring or
Diverse Pathways in Catalytic Reactions of Propargyl Aryldiazoacetates: Selectivity between Three Reaction Sites
Qiu, Huang,Deng, Yifan,Marichev, Kostiantyn O.,Doyle, Michael P.
, p. 1584 - 1590 (2017/02/10)
Three catalyst-dependent divergent reaction pathways for reactions of propargyl aryldiazoacetates are disclosed. Transition metal catalysts including those of rhodium(II), palladium(0 and II), silver(I), mercury(II), copper(I and II), platinum(II), and cationic gold(I) are effective for reactions that proceed through dinitrogen extrusion, carbene/alkyne metathesis, and aromatic substitution to form fused indeno-furanones, and use of tetrakis(acetonitrile)copper(I) provides indeno-furanones in the highest product yields. A Lewis acid catalyzed pathway that forms furan-2-ones is uncovered with FeCl3, ZnBr2, and BF3·Et2O as catalysts that proceed through activation of the aryldiazoacetate ester for arylpropargyl cation dissociation followed by recombination through cation addition to the diazo carbon. Neutral gold catalysts selectively activate the triple bond of propargyl aryldiazoacetates, resulting in the formation of allenic aryldiazoesters that further undergo uncatalyzed rearrangement.
Waste-free catalytic propargylation/allenylation of aryl and heteroaryl nucleophiles and synthesis of naphthopyrans
McCubbin, J. Adam,Nassar, Costa,Krokhin, Oleg V.
experimental part, p. 3152 - 3160 (2011/10/30)
A general method for the substitution of propargylic alcohols with electron-rich aromatic carbocycles and heterocycles has been developed. The reaction occurs under simple, mild conditions, and employs an inexpensive environmentally benign and recoverable
Unexpected reactivity of 3-(phenylethynyl)-1H-indenes towards nucleophiles: Noncatalytic addition to triple bond with or without double bond migration
Ivchenko,Nifant'ev,Luzikov,Mkoyan
, p. 1038 - 1046 (2008/02/02)
When studying the chemical properties of (3-phenylethynyl)-1H-indenes, a new reaction was discovered, namely, nucleophilic addition to conjugated enynes accompanied in some cases by migration. The reaction takes place under mild conditions and is not cata
Palladium-catalyzed cross-coupling reaction of ethynylstibanes with organic halides
Kakusawa, Naoki,Yamaguchi, Kouichiro,Kurita, Jyoji
, p. 2956 - 2966 (2007/10/03)
The reaction of ethynylstibanes (1a-g) with vinyl halides or triflate in the presence of a palladium catalyst led to the formation of cross-coupling products (5a-g, 10-12) in good to moderate yield, along with homo-coupling products (6a-g). A similar reaction of ethynyldiphenylstibane (1a) with aryl iodides (13a-i) also gave cross-coupling products (14a-i), although the yields were relatively low. The yields of the cross-coupling products were highly dependent on the nature of the solvent employed, and good results were obtained when the reaction was carried out in HMPA or amines such as diethylamine and morpholine. The results imply that HMPA and amine used as solvents facilitate transmetallation of the ethynyl group on 1 to the palladium by intermolecular coordination between antimony and oxygen (for HMPA) or nitrogen (for amine).
A new coupling reaction of propargyl carbonates mediated by Ti(OiPr)2Cl2/Mg
Yang, Fanglong,Zhao, Gang,Ding, Yu,Zhao, Zongbao,Zheng, Yueqing
, p. 1289 - 1293 (2007/10/03)
A new homocoupling reaction of 1,1-disubstituted propargyl carbonates or 1-monosubstituted propargyl carbonates, mediated by Ti(OiPr)2Cl2/Mg in ether at 0°C, was found to form symmetric 1,5-hexadiynes and 1-allenyl-5-ynes in moderate
REACTIONS OF PHTHALIMIDONITRENE WITH CONJUGATED ENAMINES. SYNTHESIS OF 1-AMINO-2-ETHYNYLAZIRIDINE
Belov, V. N.,Denisov, V. R.,Kuznetsov, M. A.
, p. 868 - 870 (2007/10/02)
Addition of phthalimidonitrene to 1-(1-octynyl)- and 1-(phenylethynyl)-cyclopentene takes place exclusively at the double bond to give the bicyclic N-phthalimidoaziridines in 40percent yield.
Cycloaddition Reactions of Allenyl Cations with Cyclopentadiene
Mayr, Herbert,Halberstadt-Kausch, Inge K.
, p. 3479 - 3515 (2007/10/02)
Propargyl halides R1-C=-C-CR2R3X (14) and cyclopentadiene react with zinc halide catalysis in ether/dichloromethane solution to give 3-halogenobicycloocta-2,6-dienes 13 (R1 = alkyl) or 5-(α-halogenobenzylidene)norbornenes 15 (R1 = aryl).The reactions are interpreted by stepwise - and -cycloadditions of intermediate allenyl cations 1, proceeding via propargylcyclopentenyl cations 5 and bicyclic vinyl cations 9 or 12.If the reactions are initiated by equimolar amounts of silver trifluoroacetate, quenching products of all postulated intermediates are isolated.The relative energies of the intermediate carbenium ions are estimated on the basis of force field calculations and of gas phase stabilities of simple carbocations.Stereochemical studies indicate that the addition reactions proceed via the compact transition state 42 rather than 41.The zinc chloride catalysed reaction of propargyl chloride 14e with cyclopentadiene yields the 2:1 product 17 (structurally assigned by X ray analysis) in addition to the 1:1 product 15e.The formation of 17 is rationalised by a -cycloaddition of allenyl cation 1 with cyclopentadiene.
