676-22-2

Basic information

• Product Name: TRANS,TRANS,TRANS-1,5,9-CYCLODODECATRIENE
• Synonyms: (1E,5E,9E)-1,5,9-Cyclododecatriene;all-trans-1,5,9-Cyclododecatrien;1,5,9-Cyclododecatriene,(1E,5E,9E)-;trans,trans,trans-1,5,9-Cyclododecatriene 99%;trans,trans,trans-1,5,9-Cyclododecatriene, stabilized with 30 to 50ppm 4-tert-butylcatechol;CYCLODODECATRIENE-1,5,9;1,5,9-BUTADIENE TRIMER;(1E,5E,9E)-1,5,9-CYCLODECATRIENE
• CAS NO: 676-22-2
• Molecular Formula: C₁₂H₁₈
• Molecular Weight: 162.27
• EINECS: 225-533-8
• Product Categories: Organic Building Blocks;Alkenes;Cyclic
• Mol File: 676-22-2.mol
• Article Data: 23

Chemical Properties

• Melting Point: 33-35 °C(lit.)
• Boiling Point: 237-238 °C(lit.)
• Flash Point: 178 °F
• Appearance: /
• Density: 0.89 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0551mmHg at 25°C
• Refractive Index: 1.5082 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Benzene (Sparingly), Hexanes (Slightly)
• BRN: 969880
• CAS DataBase Reference: TRANS,TRANS,TRANS-1,5,9-CYCLODODECATRIENE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS,TRANS,TRANS-1,5,9-CYCLODODECATRIENE(676-22-2)
• EPA Substance Registry System: TRANS,TRANS,TRANS-1,5,9-CYCLODODECATRIENE(676-22-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2518 6.1/PG 3
• WGK Germany: 3
• RTECS: GU2310000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 676-22-2(Hazardous Substances Data)

Usage

Uses

trans,trans,trans-1,5,9-Cyclododecatrene is used in method for separation and purification of cyclododecatriene.

General Description

trans,trans,trans-1,5,9-Cyclododecatriene (ttt-cdt) acts as ligand and forms rare copper complexes. Photorearrangements of CuCl complexes of ttt-cdt has been investigated.

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

Synthetic route

3-(triphenylstannyl)-all-trans-1,5,9-cyclododecatriene (98700-23-3) → (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) + tetraphenylstannan

Conditions	Yield
With phenyllithium In diethyl ether; benzene for 1h; Ambient temperature;	A 99% B n/a

cis-,cis-,cis-C12H18Ni (548757-71-7, 39330-67-1, 33154-75-5, 12126-69-1, 548757-70-6) → (Z,Z,Z)-1,5,9-cyclododecatriene (4736-48-5) + cis,cis,trans-1,5,9-cyclododecatriene (2765-29-9) + tetracarbonyl nickel (13463-39-3, 71564-36-8) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With carbon monoxide mixture of cyclododecatrienes-1,5,9: 98 % cis-,cis-,cis-; 1,3 % trans-,trans-,trans-; 0.4 % trans-,cic-,cis-;	A 98% B 0.4% C n/a D 1.3%
With CO mixture of cyclododecatrienes-1,5,9: 98 % cis-,cis-,cis-; 1,3 % trans-,trans-,trans-; 0.4 % trans-,cic-,cis-;	A 98% B 0.4% C n/a D 1.3%

trans-,trans-,cis-C12H18NiP(C6H11-cyclo)3 (37249-40-4) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + cis,cis,trans-1,5,9-cyclododecatriene (2765-29-9) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With carbon monoxide	A 97.8% B 0.3% C 0.2%
With CO	A 97.8% B 0.3% C 0.2%

trans-,trans-,trans-C12H18NiP(C6H11-cyclo)3 → cis,cis,trans-1,5,9-cyclododecatriene (2765-29-9) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With carbon monoxide	A 2.5% B 97%
With CO	A 2.5% B 97%

3-(triphenylplumbyl)-all-trans-1,5,9-cyclododecatriene (98700-24-4) → (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) + tetraphenylplumban

Conditions	Yield
With phenyllithium In diethyl ether; benzene at -65℃; for 0.5h;	A 85% B n/a

Cyclohepta-1,3,5-triene (544-25-2) + buta-1,3-diene (106-99-0) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + bicyclo<4.4.1>undeca-2,4,8-triene (86067-58-5) + 7-endo-vinyl-bicyclo<4.2.1>nona-2,4-diene (94400-08-5) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
diethylaluminium chloride; titanium tetrachloride In benzene at 60℃; for 8h; Further byproducts given;	A 5% B 8% C 78% D 5%
diethylaluminium chloride; titanium tetrachloride In benzene at 60℃; for 8h; Further byproducts given;	A 7% B 11% C 70% D 6%
diethylaluminium chloride; titanium tetrachloride In benzene at 60℃; for 8h; Further byproducts given;	A 16% B 6% C 60% D 15%
diethylaluminium chloride; titanium tetrachloride In benzene at 60℃; for 8h; Further byproducts given;	A 18% B 8% C 47% D 7%

Cyclohepta-1,3,5-triene (544-25-2) + buta-1,3-diene (106-99-0) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + bicyclo<4.4.1>undeca-2,4,8-triene (86067-58-5) + 7-endo-vinyl-bicyclo<4.2.1>nona-2,4-diene (94400-08-5) + pentacyclo[7.5.0.0(2,8).0(5,14).0(7,11)]tetradeca-3,12-diene (77300-31-3) + C14H16 (77300-30-2) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
diethylaluminium chloride; titanium tetrachloride In benzene at 60℃; for 8h; <6+2> cycloadditions with dienes and acetylenes catalyzed by titanium complexes, investigation of the complex of CHT with Ti(II)(AlCl4)2 and (η6-C6H6)Ti(II)(AlCl4)2;	A 5% B 8% C 78% D 3% E 1% F 5%

Cyclohepta-1,3,5-triene (544-25-2) + buta-1,3-diene (106-99-0) → bicyclo<4.4.1>undeca-2,4,8-triene (86067-58-5) + 7-endo-vinylbicyclo<4.2.1>nona-2,4-diene + pentacyclo[7.5.0.02,8.05,14.07,11]tetradecane-3,12-diene + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
diethylaluminium chloride; titanium tetrachloride Further byproducts given;	A 8% B 78% C 5% D 5%

buta-1,3-diene (106-99-0) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + 4-ethenylcyclohexene (100-40-3) + cis,cis,trans-1,5,9-cyclododecatriene (2765-29-9) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With bis(acetylacetonate)nickel(II); diethyl(ethoxy)aluminum at 35℃; Rate constant; other reagents;	A n/a B 6% C n/a D 17% E 74%

n-butyllithium (109-72-8, 29786-93-4) + all-trans-3-bromo-1,5,9-cyclododecatriene (14518-36-6) → 3-Butyl-all-trans-1,5,9-cyclododecatrien (98700-22-2) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
In tetrahydrofuran; hexane at -100℃; for 1h;	A 65% B 30%

all-trans-3-bromo-1,5,9-cyclododecatriene (14518-36-6) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With lithium In tetrahydrofuran for 5h; Product distribution; Heating; Br-Li exchange;	A 10% B 58%

2-vinylpyridine (100-69-6) + buta-1,3-diene (106-99-0) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + 2-(3-cyclohexenyl)pyridine (167560-56-7) + (E,E)-1,3,6-Octatriene (22038-69-3) + 4-ethenylcyclohexene (100-40-3) + 2-(1E,4E,9-decatrienyl)pyridine + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With bis(acetylacetonate)nickel(II); triethylaluminum; triphenylphosphine In benzene at 110℃; for 6h; Product distribution; other metal complexes;	A 1% B 10% C 3% D 10% E 55% F 10%

diazomethane (186581-53-3, 908094-01-9) + (trans,trans,trans-1,5,9-cyclododecatriene)nickel → bicyclo{10.1.0}-4,8-tridecadiene (15782-50-0, 5992-50-7, 1731-39-1, 15782-48-6, 15782-46-4, 15782-49-7, 15782-44-2) + bicyclo{10.3.0}-4,8-pentadecadiene (14724-87-9) + nickel (7440-02-0) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
In diethyl ether byproducts: N2; -80°C; instantaneous;	A 13% B 35% C n/a D 35%
In diethyl ether byproducts: N2; -80°C; instantaneous;	A 13% B 10% C n/a D 25%
In diethyl ether byproducts: N2; -80°C; instantaneous;	A 13% B 10% C n/a D 25%

(4E,8E,12E)-6,7,10,11-Tetrahydro-1-selena-2,3-diaza-cyclopentacyclododecene (107170-35-4) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + bicyclo<7.3.0>dodeca-2,4-dien-7-yne (107170-28-5) + (1Z,5Z,9E)-cyclododecatrien-3-yne (107170-29-6, 107170-30-9) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With copper 1.) ether 2.) 180 deg C, 20 Torr then 1 Torr;	A n/a B 3% C 3% D 12%
With copper 1.) ether 2.) 180 deg C, 20 Torr then 1 Torr;	A 12% B 3% C 3% D n/a
With copper 1.) ether 2.) 180 deg C, 20 Torr then 1 Torr;	A n/a B 3% C 3% D n/a

buta-1,3-diene (106-99-0) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
(η6-C6H6)Ti(AlCl4)2; alkali chloride at 50 - 100℃; under 1E-05 Torr; Rate constant; Product distribution; C6H6Ti(AlBr4)2 and other alkali halogenides;
With Ti(AlCl4)2; Hexamethylbenzene; triethylaluminum In benzene at 50℃; Product distribution; var. conc. of var. reagents;
With triethylaluminum; chromyl chloride; benzene at 40℃;
With triethylaluminum; bis(acetylacetonate)nickel(II) In toluene at 80℃; for 20h;

buta-1,3-diene (106-99-0) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + 1-phenylbut-1-ene (824-90-8) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
ethylaluminum dichloride; titanium tetrachloride; triphenylphosphine In benzene at 50℃; Product distribution;

buta-1,3-diene (106-99-0) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + 4-ethenylcyclohexene (100-40-3) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With nickel(0) on various phosphite functionalized ethylene oligomer as catalyst; triethylaluminum; bis(acetylacetonate)nickel(II) In hexane; toluene at 95℃; for 5h; Product distribution;
2>Ni In toluene at 110℃; Product distribution; other polyethylene-entrapped Nickel(0) catalysts; catalytic activity;

buta-1,3-diene (106-99-0) + Bis(trimethylsilyl)ethyne (14630-40-1) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + 1,2-bis(trimethylsilyl)cyclohexa-1,4-diene + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
diethylaluminium chloride; titanium tetrachloride In benzene at 60℃; for 6h; in a sealed ampoule; Yield given;

buta-1,3-diene (106-99-0) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + (1Z,3Z,7Z)-Cyclododeca-1,3,7-triene + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With triethylaluminum; 2,2'-dipyridylmethane-Ni(OAc)2 In toluene at 80℃; for 64h; Product distribution; variation of catalyst, reaction temperature and time;

cis,cis,trans-1,5,9-cyclododecatriene (2765-29-9) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In benzene Product distribution; Heating; various reaction time; various radicals; various alkenes;

buta-1,3-diene (106-99-0) → (E)-1,3,7-octatriene (26198-79-8) + 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + (E,E)-1,3,6-Octatriene (22038-69-3) + 4-ethenylcyclohexene (100-40-3) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
With tetrakis(1,3,5-triaza-7-phosphaadamantane)palladium(0) In water at 80℃; for 20h; Product distribution; various catalysts;

triethylaluminum (97-93-8) + chromyl chloride (14977-61-8) + buta-1,3-diene (106-99-0) + benzene (71-43-2) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
at 40℃;
at 40℃;

diethylaluminium chloride (96-10-6) + titanium tetrachloride (7550-45-0) + buta-1,3-diene (106-99-0) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + 4-ethenylcyclohexene (100-40-3) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
Oligomerisierung; Einfluss vin Temperatur, Loesungsmittel, Zusammensetzung des Katalysators sowie von Zusaetzen auf diese Reaktion;

diethylaluminium chloride (96-10-6) + titanium tetrachloride (7550-45-0) + buta-1,3-diene (106-99-0) + benzene (71-43-2) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + 4-ethenylcyclohexene (100-40-3) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
at 40℃; Oligomerisierung;
at 40℃; Kinetics; Oligomerisierung;
at 40℃; Oligomerisierung;

buta-1,3-diene (106-99-0) + nickel (0)-catalyst → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + 4-ethenylcyclohexene (100-40-3) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
Oligomerisierung; Produkt5: Cyclododeca-1c,5c,9t-trien;

cis-tris-<2.2.2>-ς-homobenzene (87422-12-6) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + (Z,Z,Z)-1,5,9-cyclododecatriene (4736-48-5) + cis-5,6-Divinyl-cis-cycloocten (46045-35-6, 53264-71-4, 53264-72-5) + trans-5,6-Divinyl-cis-cycloocten (46045-35-6, 53264-71-4, 53264-72-5) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) + further byproducts

Conditions	Yield
at 450℃; Mechanism; Product distribution; other temp. were studied;

cis-tris-<2.2.2>-ς-homobenzene (87422-12-6) → (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + C12H18 (2855-27-8, 53264-67-8, 53264-68-9, 53264-69-0, 53264-70-3) + C12H18 (2855-27-8, 53264-67-8, 53264-68-9, 53264-69-0, 53264-70-3) + 1,trans-2,cis-4-trivinylcyclohexane (2855-27-8, 53264-67-8, 53264-68-9, 53264-69-0, 53264-70-3) + C12H18 (2855-27-8, 53264-67-8, 53264-68-9, 53264-69-0, 53264-70-3) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) + further byproducts

Conditions	Yield
at 500℃; Mechanism; Product distribution; other temp. were studied;

(2E,6E,10E)-Cyclododeca-2,6,10-trienone → (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
Multi-step reaction with 3 steps 3: Cu powder / 1.) ether 2.) 180 deg C, 20 Torr then 1 Torr View Scheme

C13H19N3O → (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Conditions	Yield
Multi-step reaction with 2 steps 2: Cu powder / 1.) ether 2.) 180 deg C, 20 Torr then 1 Torr View Scheme

(1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → trans-1,2-epoxy-trans,trans-5,9-cyclododecadiene (42539-84-4)

Conditions	Yield
With tert.-butylhydroperoxide; hexacarbonyl molybdenum In benzene at 80℃; for 6h;	87.6%

trans-,cis-,cis-C12H18NiP(OC6H4C6H5-o)3 + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → trans-,trans-,trans-C12H18NiP(OC6H4C6H5-o)3

Conditions	Yield
	85%
	85%

chloroform (67-66-3) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → trans,trans-13,13-Dichloro-trans-bicyclo<10.1.0>trideca-4,8-diene (4413-92-7, 5775-25-7, 23720-52-7, 85611-71-8)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 45℃; for 3h;	82%

rhodium(III) chloride trihydrate + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → catena-poly-[μ-dichloro-(1,2,12-η)-1,5,8-cyclododecatrienylrhodium]

Conditions	Yield
In ethanol byproducts: C12H20, C12H22; Ar-atmosphere; closed vessel, 80°C, 8 h; collection (filtration), washing (EtOH), drying (vac.); elem. anal.;	82%

N-Nitrosodimethylamine (62-75-9) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → syn-1-hydroxyimino-2-dimethylamino-trans,trans-cyclododeca-5,9-diene (83638-04-4)

Conditions	Yield
With hydrogenchloride In methanol for 4h; Irradiation;	76%

bis(acetylacetonate)nickel(II) + diethyl(ethoxy)aluminum (1586-92-1) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → (trans,trans,trans-1,5,9-cyclododecatriene)nickel

Conditions	Yield
In diethyl ether at about 0°C; recrystn. from ether;	75%
In diethyl ether at about 0°C;	57%
In diethyl ether at about 0°C;	57%

(1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → (1R*,2R*,5R*,6R*,9S*,10S*)-cyclododecane-1,2,5,6,9,10-hexaol + (1R*,2R*,5R*,6R*,9R*,10R*)-cyclododecane-1,2,5,6,9,10-hexaol

Conditions	Yield
With osmium(VIII) oxide; N-methyl-2-indolinone In water; acetone for 0.25h; Ambient temperature; Yields of byproduct given;	A 72% B n/a
With osmium(VIII) oxide; N-methyl-2-indolinone In water; acetone for 0.25h; Ambient temperature; Yield given;	A 72% B n/a

(1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → (4E,8E)-dodeca-4,8-diene-1,12-diol (131392-77-3)

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In dichloromethane for 24h; Ambient temperature;	71%
Multi-step reaction with 3 steps 1: N-methyl-morpholine-N-oxide; water / OsO4 / CH2Cl2 / 20 °C 2: NaIO4; water / CH2Cl2; acetone 3: NaBH4 / methanol / 0 °C View Scheme

silver(I) hexafluorophosphate (26042-63-7) + [Pd(CH2CH(C6H5)C5(CH3)5)Cl]2 (43064-53-5, 38960-16-6) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → [Pd(1,2-bis(diphenylphosphino)ethane)(η(3)-cyclododecadienyl)][PF6]

Conditions	Yield
With 1,2-bis-(diphenylphosphino)ethane In not given byproducts: AgCl; N2-atmosphere; treatment of Pd-complex with AgPF6 and diphosphine, then with triene; elem. anal.;	71%

dodecacarbonyl-triangulo-triruthenium (15243-33-1) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → [Ru3H(CO)9(C12H17)]

Conditions	Yield
In hexane reflux (8 h); column chromy., then thin-layer chromy., crystn. (n-hexane);	70%

diborane (19287-45-7) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → dodecahydro-9b-bora-phenalene (1130-59-2, 2938-53-6, 16664-33-8)

Conditions	Yield
With diethylene glycol dimethyl ether; triethylamine In tetrahydrofuran at 130 - 200℃; for 6h; Inert atmosphere;	68%

tetrafluoroboric acid diethyl ether (67969-82-8) + thianthrene-5-oxide (2362-50-7) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → C24H25S2(1+)*BF4(1-)

Conditions	Yield
With trifluoroacetic anhydride In acetonitrile at 0℃; for 0.75h; Inert atmosphere; regioselective reaction;	68%

bis(acetylacetonate)nickel(II) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → (trans,trans,trans-1,5,9-cyclododecatriene)nickel

Conditions	Yield
With samarium diiodide In tetrahydrofuran under N2; a soln. of Ni-contg. compd. and a ligand in THF was treated dropwise with a THF soln. of SmI2 at -20°C; addn. of SmI2 was continued until no more color change occurred; warming to room temp.; after stirring for 1 h, the solvent was removed in vac.; extn. with toluene; the soln. was filtered through a column of Celite; the solvent was removed in vac.;	61%
With diethylaluminumethoxide In tetrahydrofuran according to Bogdanovic B., et al., Justus Liebigs Ann. Chem., 1966, 699, 1; mixt. of Ni compd., cyclododecatriene and Al compd. was reacted in THF; sublimed (vac.);

acetic acid (64-19-7) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → (E,E,E)-2,6,10-cyclododecatrienoic acid ester (14296-71-0)

Conditions	Yield
With manganese(IV) oxide; p-benzoquinone; palladium diacetate at 40℃; for 72h;	60%

(1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → (4E,8E)-dodeca-4,8-dienedial (60391-93-7)

Conditions	Yield
Stage #1: (1E,5E,9E)-cyclododeca-1,5,9-triene With osmium(VIII) oxide; 4-methylmorpholine N-oxide Inert atmosphere; Stage #2: With sodium periodate; silica gel Inert atmosphere;	59%
(i) O3, AcOH, (ii) Zn; Multistep reaction;
(i) O3, cyclohexane, MeOH, (ii) H2, Lindlar catalyst, dioxane; Multistep reaction;
Multi-step reaction with 2 steps 1: N-methyl-morpholine-N-oxide; water / OsO4 / CH2Cl2 / 20 °C 2: NaIO4; water / CH2Cl2; acetone View Scheme

bis(acetylacetonate)nickel(II) + trimethylaluminum (75-24-1) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → (trans,trans,trans-1,5,9-cyclododecatriene)nickel

Conditions	Yield
In diethyl ether -40°C;	57%
In diethyl ether -40°C;	57%
In hexane -40°C;	41.7%
In hexane -40°C;	41.7%

bis(acetylacetonate)nickel(II) + triethylaluminum (97-93-8) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → (trans,trans,trans-1,5,9-cyclododecatriene)nickel

Conditions	Yield
In diethyl ether -40°C;	57%
In diethyl ether -40°C;	57%
In hexane -40°C;	41.7%
In hexane -40°C;	41.7%

(1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → (5E,9E)-(1R,2R)-Cyclododeca-5,9-diene-1,2-diol (5202-25-5, 15786-26-2, 29118-70-5, 122674-42-4, 122674-45-7)

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In dichloromethane	53%

Upstream product

• 2765-29-9 cis,cis,trans-1,5,9-cyclododecatriene 
• 97-93-8 triethylaluminum 
• 14977-61-8 chromyl chloride 
• 106-99-0 buta-1,3-diene 
• 71-43-2 benzene 
• 96-10-6 diethylaluminium chloride 
• 7550-45-0 titanium tetrachloride 
• 51097-60-0 (Z)-oct-4-enedial 
• 15546-42-6 [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide 
• 4526-07-2 1,4-bis(trimethylsilyl)-1,3-butadiyne 
• 548757-70-6 [Ni(1,5,9-cyclododecatriene)] 
• 706-31-0 (1E,5E,9Z)-cyclododeca-1,5,9-triene 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 37249-40-4 trans-,trans-,cis-C₁₂H₁₈NiP(C₆H₁₁-cyclo)3 

Downstream Products

• 1130-59-2 dodecahydro-9b-bora-phenalene 
• 706-31-0 (1E,5E,9Z)-cyclododeca-1,5,9-triene 
• 5202-25-5 (5E,9E)-(1R,2R)-Cyclododeca-5,9-diene-1,2-diol 
• 2855-27-8 1.2.4- trivinylcyclohexane 
• 14800-42-1 trans,trans,trans-Cyclododecatrien-(2,6,10)-yl-N-phenyl-urethan 
• 6221-92-7 cyclododecyl acetate 
• 909767-36-8 Acetic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,5R)-5-[(R)-4-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-butyl]-tetrahydro-furan-2-yl}-butyl ester 
• 909767-35-7 cis-4-(tert-butyldiphenylsiloxy)-1-{5-[4-(tert-butyldiphenylsiloxy)-1-hydroxybutyl]tetrahydrofuran-2-yl}butan-1-ol 
• 909767-34-6 C₄₄H₅₈O₂Si₂ 
• 830-13-7 cyclododecanone 
• 131392-71-7 Toluene-4-sulfonic acid (4E,8E)-1-(2-[1,3]dioxolan-2-yl-ethyl)-trideca-4,8-dienyl ester 
• 131392-62-6 (4E,8E)-1,1-dimethoxy-12-tosyloxy-4,8-dodecadiene 
• 54899-57-9 3(4)-Phenyltricyclo<6.4.0.0^2.6>dodecan 
• 67923-54-0 cyclododeca-4,8-dien-1-yl acetate 

Relevant articles and documents

(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.

16-Electron Nickel(0)-Olefin Complexes in Low-Temperature C(sp2)-C(sp3) Kumada Cross-Couplings

Investigations into the mechanism of the low-temperature C(sp2)-C(sp3) Kumada cross-coupling catalyzed by highly reduced nickel-olefin-lithium complexes revealed that 16-electron tris(olefin)nickel(0) complexes are competent catalysts for this transformation. A survey of various nickel(0)-olefin complexes identified Ni(nor)3as an active catalyst, with performance comparable to that of the previously described Ni-olefin-lithium precatalyst. We demonstrate that Ni(nor)3, however, is unable to undergo oxidative addition to the corresponding C(sp2)-Br bond at low temperatures (a nickel(0)-alkylmagnesium complex. We demonstrate that this unique heterobimetallic complex is now primed for reactivity, thus cleaving the C(sp2)-Br bond and ultimately delivering the C(sp2)-C(sp3) bond in high yields.

Indenylidene complexes of ruthenium bearing NHC ligands - structure elucidation and performance as catalysts for olefin metathesis

Second-generation catalysts of the general formula Cl2Ru-(SIMes) (L)(3-phenylinden-1-ylidene), 3a (L = PCy3), 3b (L =PPh3), 3c (L = py), and Cl2Ru(SIMe)(L)(3-phenylinden-1-yl-idene), 4a (L = PCy 3), 4b (L = PPh

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