706-31-0

Usage

Uses

Used in Organometallic Chemistry:
TRANS,TRANS,CIS-1,5,9-CYCLODODECATRIENE is used as a ligand in organometallic chemistry for its ability to form stable complexes with metal atoms. This property allows for the development of new catalysts and materials with enhanced properties.
Used in Chemical Synthesis:
TRANS,TRANS,CIS-1,5,9-CYCLODODECATRIENE is used as a precursor in the production of various industrial chemicals. Its unique structure and reactivity make it a valuable building block for synthesizing complex organic compounds.
Used in Pharmaceutical Applications:
TRANS,TRANS,CIS-1,5,9-CYCLODODECATRIENE is used as a starting material in the synthesis of pharmaceutical compounds due to its potential biological activity and chemical versatility.
Used in Polymer Industry:
TRANS,TRANS,CIS-1,5,9-CYCLODODECATRIENE is used as a monomer in the production of polymers, contributing to the development of new materials with improved properties.
Used in Chemical Research:
TRANS,TRANS,CIS-1,5,9-CYCLODODECATRIENE is used as a model compound in chemical research to study the properties and reactions of cyclic hydrocarbons and their derivatives. This helps in understanding the fundamental aspects of organic chemistry and the development of new synthetic methods.

InChI:InChI=1/C12H18/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-2,7-10H,3-6,11-12H2/b2-1-,9-7-,10-8+

Upstream product

• 106-99-0 buta-1,3-diene 
• 14518-36-6 all-trans-3-bromo-1,5,9-cyclododecatriene 
• 107170-35-4 (4E,8E,12E)-6,7,10,11-Tetrahydro-1-selena-2,3-diaza-cyclopentacyclododecene 
• 2765-29-9 cis,cis,trans-1,5,9-cyclododecatriene 
• 97-93-8 triethylaluminum 
• 14977-61-8 chromyl chloride 
• 71-43-2 benzene 
• 96-10-6 diethylaluminium chloride 
• 7550-45-0 titanium tetrachloride 
• 548757-70-6 [Ni(1,5,9-cyclododecatriene)] 
• 101-02-0 triphenyl phosphite 
• 676-22-2 (1E,5E,9E)-cyclododeca-1,5,9-triene 
• 51097-60-0 (Z)-oct-4-enedial 
• 15546-42-6 [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide 

Downstream Products

• 5775-26-8 trans,trans-9,9,14,14-Tetrachlor-tricyclo<11.1.0.0^8.10>tetradecen-(4-cis) 
• 15786-37-5 dodeca-4c,8t-dienedial 
• 3194-55-6 1,2,5,6,9,10-hexabromocyclododecane 
• 5202-25-5 cyclododeca-5c,9t-diene-1r,2c-diol 
• 1130-59-2 cis-perhydro-9b-boraphenalene 
• 77089-36-2 10,17-Diphenyl-9,18-di(p-bromobenzoyl)-6,11-dioxa-10,17-diazatricyclo<13.3.0.0^8,12>octadec-Z-4-ene 
• 42539-84-4 trans-1,2-epoxy-trans,trans-5,9-cyclododecadiene 
• 943-93-1 (Z,E)-5,9-Cyclododecadiene (E)-1,2-epoxide 
• 294-62-2 cyclododecane 
• 1129-89-1 cis-cyclododecene 
• 1486-75-5 (E)-Cyclododecen 
• 1684-05-5 trans,trans-1,5-cyclododecadiene 
• 1076-17-1 hexahydroindacene 
• 2146-36-3 decahydroacenaphthene 

Relevant academic research and scientific papers

Synthesis of (14C6-3,4,7,8,11,12)-(1E,5E,9E)- cyclododeca-1,5,9-triene

Trimerization of butadiene in the presence of Ni(0) affords (1E,5E,9E)-cyclododeca-1,5,9-triene 1 (ttt-CDT), (1E,5E,9Z)-cyclododeca-1,5,9- triene 2 (ttc-CDT), and other isomers/oligomers. After optimization of reaction conditions, [14C6-3,4,7,8,11,12]-ttt-CDT 1 was synthesized efficiently either by homogenous or heterogeneous Ni(0) catalytic trimerization of [1,4-14C2]butadiene 10, in 60-82% yield. Depending on the exact reaction conditions employed, the yields and ratio of 1/2 ranged from (59-90%) / (41-10%). The all-trans isomer was conveniently isolated via Ag +-mediated reversed-phase HPLC. The important intermediate [1,4- 14C2]-1,3-butadiene 10 was prepared from potassium [ 14C]cyanide and 1,2-dibromoethane 3 as starting materials, in seven steps with a 57% yield. The total radioactive yield of [14C 6-3,4,7,8,11,12]-ttt-CDT 1 is 30% from [14C]KCN. Copyright

A new method of synthesis of cyclododecyl ethers

Cyclododecyl ethers were synthesized by substitutive alkoxylation of isomeric acetoxycyclododeca-2,6,10-trienes with aliphatic alcohols in the presence of Pd[PPh3]4, followed by hydrogenation of the double bonds. The kinetics of the substitutive alkoxylation of isomeric cyclododecatrien-1-yl acetate with 2-methoxyethanol at 358°C were studied.

Nickel(0) and palladium(0) complexes with 1,3,5-triaza-7-phosphaadamantane. Catalysis of buta-1,3-diene oligomerization or telomerization in an aqueous biphasic system

New homoleptic nickel(0) and palladium(0) complexes with a water-soluble ligand, 1,3,5-triaza-7-phosphaadamantane, were prepared and characterized by 1H, 13C, and 31P NMR spectra. The complexes, together with the known ana

Titanium-catalyzed [4+2] and [6+2] cycloadditions of 1,4-bis(trimethylsilyl)buta-1,3-diyne

The (C2H5)2AlCl/TiCl4 catalyst induces the [4+2] cycloaddition of butadiene or the [6+2] cycloaddition of 1,3,5-cycloheptatriene (CHT) to individual acetylenic moieties of 1,4-bis(trimethylsilyl)buta-1,3-diyne (BSD). Heating of the 2:1 butadiene adduct, bis(2-trimethylsilylcyclohexa-1,4-dien-1-yl), to 250°C yields 2,2′-bis(trimethylsilyl)biphenyl. The 1:1 adduct of BSD with CHT, 7-trimethylsilyl-8-trimethylsilylethynylbicyclo[4.2.1]nona-2,4-diene, is obtained as virtually the only product if the initial molar ratio CHT:BD equal to 1.86 is used.

(Z)-(E) Interconversion of Olefins by the Addition-Elimination Sequence of the (TMS)3Si(.) Radical

Tris(trimethylsilyl) radical is effective inisomerizing either acyclic or cyclic olefins by an addition-elimination sequence.The E/Z ratio after equilibration generally reflects the thermodynamic stability of (Z)- and (E)-alkenes.It has been shown for (E)- and (Z)-hexen-1-ol that equilibration (Z/E = 18/82) is reached with the (TMS)3Si(.) radical in 10 h at 80 deg C, whereas with PhS(.) and Bu3Sn(.) radicals the same isomeric composition is reached in 1 and 4 h, respectively.In cyclic systems like (Z)-cyclododecene the ratio of Z/E = 46/54 is reached in 8 h, while with PhS(.) and Bu3Sn(.) it is much slower.An explanation of this phenomenon has been advanced.Additional information on the impact of this addition-elimination methodology in organic synthesis is given.

The crystal structure of (η6-C6Me6)Ti2 and the catalytic activity of the (C6Me6)TiAl2Cl8-xEtx (x = 0-4) complexes towards butadiene

The composition of (C6Me6)TiAl2Cl8-xEtx complexes in (C6Me6)TiAl2Cl8 + n Et3Al (n = 0.5-6) systems was studied by UV-Vis spectroscopy and the X-ray crystal structure of one of them, (η6-C6Me6)Ti2 (IIa-2), has been determined.The complex crystallizes in the orthorhombic space group Pna21 with Z = 4 and lattice parameters a 15.634(3), b 11.355(2), c 14.417(a) Angstroem.The ethyl groups of IIa-2 reside in outer positions of aluminate ligands farther away from the C6Me6 ligand.The other part of the complex does not differ remarkably from structures of other (arene)TiII complexes.Negligible activity of (C6Me6)TiAl2Cl8 towards the butadiene cyclotrimerization is considerably increased by addition of 2.5-3.0 equivalents of Et3Al.As follows from UV-Vis spectra, such systems contain mainly the (C6Me6)TiAl2Cl5Et3 complex.It is suggested that the introduction of three Et substituents destabilizes the Ti-(η6-C6Me6) bond so that the replacement of hexamethylbenzene by butadiene in the first step of a catalytic cycle becomes more feasible.

EFFECT OF TRIPHENYLPHOSPHINE ON THE CYCLOTRIMERIZATION OF BUTADIENE CATALYZED BY THE TiCl4-EtAlCl2 SYSTEM

Addition of PPh3 to the TiCl4 + n EtAlCl2 (n = 4-10) systems, which normally exhibit mostly Friedel-Crafts and polymerization activity towards butadiene, turns these systems into highly specific catalysts for the cyclotrimerization of butadiene to (Z, E, E)-1,5,9-cyclododecatriene.The effect of PPh3 lies in removal of AlCl3, which is formed in the reduction of TiCl4 with EtAlCl2 and in the disproportionation of EtAlCl2, for the AlCl3.PPh3 complex displays higher stability in comparison with the analogous complexes with ethylaluminium chlorides.The composition of the (η6-benzene)Ti(II) complexes, which are the catalytically active species, was determined by electronic absorption spectroscopy in the post-reaction mixtures.

ISOMERIZATION OF TRANS-1,2-EPOXY-CIS,TRANS-5,9-CYCLODODECADIENE, TRANS-1,2-EPOXY-TRANS,TRANS-5,9-CYCLODODECADIENE, AND TRANS-EPOXYCYCLODODECANE TO THE CORRESPONDING KETONES BY THE ACTION OF LITHIUM AND MAGNESIUM IODIDES AND BROMIDES

The isomerization of trans-1,2-epoxy-cis,trans-5,9-cyclododecadiene, trans-1,2-epoxy-trans,trans-5,9-cyclododecadiene, and trans-epoxycyclododecane by the action of lithium and magnesium iodides and bromides leads to the formation of the corresponding 12-membered cyclic ketones and is not accompanied by ring contraction.

THE INFLUENCE OF ALKALI METAL HALIDES ON THE BUTADIENE CYCLOTRIMERIZATION CATALYZED BY (BENZENE)TITANIUM(II) COMPLEXES

Addition of alkali chlorides (MCl) to (η6-C6H6)Ti(AlCl4)2 (Ia) decreases the catalytic activity of Ia while the selectivity of the (Z,E,E)-1,5,9-cyclododecatriene formation is improved only when NaCl is used at the optimum molar ratio NaCl/Ia ca 5.The alkali chlorides remove free AlCl3, which is present in the system as an admixture, probably in the form of MAlCl4 complexes; however, an excess of MCl brings about decomposition of catalytic trinuclear Ti(II) complexes during the butadiene cyclotrimerization.In addition to inactive TiCl2, this decomposition yields some AlCl3 which induces the formation of cationic byproducts, 1-phenylbut-2-ene and (E)-1,4-poly(butadiene), before it is deactivated or quenched with MCl.

Polymer supported 2,2'-dipyridylmethane: catalytic activity of transition metal complexes in hydrogenations and oligomerizations

The palladium(II) acetate complex of the chelating ligand 2,2'-dipyridylmethane supported on polystyrene-2percent divinylbenzene is an efficient catalyst for hydrogenation of alkenes and alkynes.Cyclopentadiene can be reduced with high selectivity to cyclopentene, but no selectivity is observed for the non-conjugated diene 1,5-cyclooctadiene.In the hydrogenation of 3-methylcyclohex-2-en-1-ol only small amounts of ketone are formed as a by-product, in contrast to the reaction catalysed by palladium on charcoal.Nickel(II) complexes of the same ligand catalyze the trimerization of butadiene to 1,5,9-cyclododecatrienes.