28393-07-9

Upstream product

• 100858-78-4 1-Chloro-1-decyne 
• 110-83-8 cyclohexene 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 764-93-2 1-decyne 
• 100-52-7 benzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 1601-97-4 bis-(4-iodo-phenyl)-diazene 
• 636-98-6 p-nitrobenzene iodide 
• 107-19-7 propargyl alcohol 
• 5390-04-5 pent-1-yn-5-ol 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

Microwave enhanced Glaser coupling under solvent free conditions

A microwave enhanced, solvent free, Glaser coupling reaction has been developed. Self coupling of terminal alkynes on potassium fluoride-alumina in the presence of cupric chloride affords good yields of the corresponding diacetylenes.

Tetraalkynylstannanes in the Stille cross coupling reaction: a new effective approach to arylalkynes

The Stille-type cross coupling reaction with tetraalkynylstannanes was studied in detail for the first time. The reaction provides a simple and effective route towards a variety of arylalkynes. The advantages and limitations of the proposed procedure are discussed.

Synthesis and Properties of New Dimeric η2-Diyne Complexes of Cobalt Linked through an Azobenzene Ligand

The reaction between 4,4′-diiodoazobenzene (0) with excess trimethylsilylacetylene or dec-1-yne in the presence of catalytic amounts of PdCl2(PPh3)2 and CuI, Sonogashira coupling conditions, gave rise to the formation of 4,4′-bis(trimethylsilylethynyl)azobenzene (1) and 4,4′-bis(dec-1-ynyl)azobenzene (2), in good yield, in addition to icosa-9,11-diyne (3) as byproduct in the last case. The analogous reactions from 0 and the alkynyl-cobalt complexes Co2(CO)4(μ-L-L)(μ2-η2-SiMe3C2)](C≡CH) (L-L = dppm, dmpm) afforded 12-14. Complexes 4-7 and 15 have been obtained by direct reaction between Co2(CO)8 and the organic ligands 1-3. In order to increase the stabilization of Co-Co bonds, diphenylphosphinomethane-substituted alkyne-carbonyl complexes 8-11 were prepared by substitution reaction of carbonyl ligands in the presence of Me3NO at the Co2(CO)6 units from 4-7. All products were characterized by analytical and spectroscopic data (IR, 1H, 13C, and 31P NMR, and MS). Crystals of 9 suitable for single-crystal X-ray diffraction were grown, and the molecular structure of this compound is discussed. In this paper we report a comparative electrochemical study of these complexes by means of cyclic and square-wave voltammetry techniques, the trans-cis photoisomerization study of azobenzene compounds, and the thermotropic liquid-crystalline behavior. (Chemical Equation Presented).

Mild-condition synthesis of allenes from alkynes and aldehydes mediated by tetrahydroisoquinoline (THIQ)

A practical 1,2,3,4-tetrahydroisoquinoline (THIQ)-mediated synthesis of 1,3-disubstituted allenes from terminal alkynes and aldehydes under mild conditions in the presence of CuBr first and then ZnI2 was reported. This telescoped allene synthes

Fast, ligand- and solvent-free synthesis of 1,4-substituted buta-1,3-diynes by cu-catalyzed homocoupling of terminal alkynes in a ball mill

A method for the Glaser coupling reaction of alkynes by using a vibration ball mill has been developed. The procedure avoids the use of ligands and solvents during the reaction. Aryl- and alkyl-substituted terminal alkynes undergo homocoupling if coground with KF-Al2O3 and CuI as a milling auxiliary and catalyst. Furthermore, an alternative protocol has been developed incorporating 1,4-diazabicyclo[2.2.2]octane (DABCO) as an additional base allowing the use of KF-Al2O3 with a lower KF loading. Besides Cu salts, the homocoupling of phenylacetylene is also catalyzed by Ni or Co salts, as well as by PdCl2. TMS-protected phenylacetylene could be directly converted into the homocoupling product after in situ deprotection of the alkyne by fluoride-initiated removal of the trimethylsilyl group.

New irreversible thermochromic polydiacetylenes

New diacetylenic compounds are described. These compounds are unfunctionalised, monoalcohols, diols or monoesters and present irreversible thermochromic behaviour. When heated, these diynes change colour from blue to red in temperature ranging between -50 and +75 °C depending on chain lengths. A relationship between the number of atoms and the thermochromism temperature has been highlighted. Moreover, a mechanism of this thermochromic phenomenon is demonstrated based on Raman spectroscopy, ESR and solid NMR.

On the heck reaction of 1-chloroalk-1-ynes - Synthesis and characterization of 1,3-disubstituted 7-(Prop-2-ynylidene)bicyclo[2.2.1]heptanes and other bicycles

The Heck reaction of cyclohexene with 1-chloroalk-1-ynes ClC≡CR 1 (R = Ph a, c-Hex b, n-Bu c, n-Oct d) 1) using [Pd(OAc)2]/NaO2CH/[NEt3Bz]Cl as catalyst system (DMF, 25°C) affords 1,3-disubstituted 7-(prop-2-ynylidene)bicyclo[2.2.1]heptanes 2 as tandem products by reaction of cyclohexene and ClC≡CR in a ratio of 1:2. To a smaller extent, substituted 7-[(cyclohexenyl)methylidene]bicyclo- [2.2.1]heptanes 3 (tandem products by reaction of cyclohexene and ClC≡CR in a ratio of 2:1) and the regular Heck products (alkynylcyclohexenes 4) are formed. The homocoupling of 1 to give RC≡C-C≡CR does not take place, except for R = n-Oct where it proceeds as side reaction. The analogous reaction of ClC≡CR with cycloheptene affords the 2:1 products (substitued 8-[(cycloheptenyl)methylidene]bicyclo[3.2.1]octanes 6) as main products and the 1:2 products (1,3-disubstituted 7-(prop-2-ynylidene)bicyclo[3.2.1]-octanes 5) as well as the regular Heck products (alkynylcycloheptenes 7) as side products. The ratio 5:6 is strongly influenced by the ratio cylcoheptene:1. The products 2, 5a and 6 were isolated and characterized by means of 1H and 13C NMR spectroscopy. The molecular structures of 7-(1,3-diphenylprop-2-ynylidene)bicyclo[2.2.1]heptane (2a) and 8-[(cyclo-heptenyl)phenylmethylidene)]bicyclo[3.2.1]octane (6a) (as mixture of the cyclohept-3- and -4-enyl double bond isomers) were determined by single-crystal X-ray structure analysis. WILEY-VCH Verlag GmbH, 1999.