592-42-7

Basic information

• Product Name: 1,5-Hexadiene
• Synonyms: hexa-1,5-diene;Diallyl;Biallyl
• CAS NO: 592-42-7
• Molecular Formula: C₆H₁₀
• Molecular Weight: 82.16
• EINECS: 209-754-7
• Mol File: 592-42-7.mol

Chemical Properties

• Melting Point: -141℃
• Boiling Point: 60 °C(lit.)
• Flash Point: −17 °F
• Appearance: clear colorless to slightly yellow liquid
• Density: 0.697 g/cm³
• Vapor Pressure: 226mmHg at 25°C
• Refractive Index: 1.411
• CAS DataBase Reference: 1,5-Hexadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Hexadiene(592-42-7)
• EPA Substance Registry System: 1,5-Hexadiene(592-42-7)

Safety Data

• Hazard Codes: F:Highly flammable
• Statements: R11:Highly flammable.; R36/37:Irritating to eyes and respiratory system.
• Safety Statements: S16:Keep away from sources of ignition - No smoking.
• Hazardous Substances Data: 592-42-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H10/c1-3-5-6-4-2/h3-4H,1-2,5-6H2

Synthetic route

1,2-epithio-5-hexene (6766-70-7) → 1,5-Hexadien (592-42-7)

Conditions	Yield
With hydrogen sulfide; triphenylphosphine; methyltrioxorhenium(VII) In [D3]acetonitrile for 1h; Ambient temperature;	100%

cis-1,2-Bis(iodomethyl)cyclobutane (77774-05-1) → 1,5-Hexadien (592-42-7)

Conditions	Yield
With tert.-butyl lithium In diethyl ether; pentane at -23℃; for 0.5h; Mechanism;	98%

dimethylacetylene (503-17-3) + Cp(η3-C3H5)2Cr → Cp(η6-Me6C6)Cr + 1,5-Hexadien (592-42-7)

Conditions	Yield
In pentane under Ar, addn. of the butyne to a suspension of the Cr complex in pentane at -78°C, stirred and allowed to warm to 0°C over 7 h (slow warming to suppress formation of hexamethylbenzene), held for 48 h; filtration, cooled to -78°C, crystn., elem. anal., the diene detn. by GC analysis;	A 94.6% B 86%

trimethyl(allyl)stannane (762-73-2) + allyl bromide (106-95-6) → 1,5-Hexadien (592-42-7)

Conditions	Yield
bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide Ambient temperature;	94%
With bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 3h;	94%

trimethyl(allyl)stannane (762-73-2) + allyl bromide (106-95-6) → 1,5-Hexadien (592-42-7) + trimethyltin bromide (1066-44-0)

Conditions	Yield
With ((π-C3H5)PdCl)2 In N,N,N,N,N,N-hexamethylphosphoric triamide room temp.;	A 94% B n/a

Cp(η3-C3H5)2Cr → Cr(η(5)-C5H5)(η(6)-cyclooctatetraene) + 1,5-Hexadien (592-42-7)

Conditions	Yield
With cyclooctatetraene In pentane under Ar, addn. of the tetraene to a suspension of the Cr complex in pentane at -78°C, stirred for 3 d at -20°C, beige suspension; evapn. to dryness, residue sublimed at 60°C, high vac., elem. anal., detn. of the diene by GC analysis;	A 85.7% B 94%

N-(4-chlorobenzylidene)aniline (2362-79-0) + allyl bromide (106-95-6) → 1,5-Hexadien (592-42-7) + 4-chloro-N-phenyl-α-2-propenylbenzenemethanamine

Conditions	Yield
With tetrabutylammomium bromide; indium(III) chloride In tetrahydrofuran chemo-electrochemical allylation;	A n/a B 93%

3,4-Dimethoxy-benzalanilin (166670-25-3) + allyl bromide (106-95-6) → 1,5-Hexadien (592-42-7) + N-[1-(3,5-dimethoxyphenyl)-3-butenyl]-N-phenylamine

Conditions	Yield
With tetrabutylammomium bromide; indium(III) chloride In tetrahydrofuran chemo-electrochemical allylation;	A n/a B 93%

Li(1+)*((H3C)2NCH2)2*(C5H5)V(C3H5)2(1-)=(Li((H3C)2NCH2)2)((C5H5)V(C3H5)2) (89184-58-7) + carbon monoxide (201230-82-2) → tetracarbonyl(η(5)-cyclopentadienyl)vanadium(I) + 1,5-Hexadien (592-42-7) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + dilithium (η-cyclopentadienyl)tri(carbonyl)vanadate

Conditions	Yield
In tetrahydrofuran reaction of CO with (LiTMEDA)(CpV(C3H5)2) in THF (Ar); formation of 1,5-hexadiene in the reaction soln., extn. of the residue with toluene, filtering off the solid and drying to give Li2(CpV(CO)3), evapn. of the filtrate to dryness and subliming the residue in a high vacuum at 80°C to give CpV(CO)4;	A 91% B 46% C n/a D n/a

Cp(η3-C3H5)2Cr + diphenyl acetylene (501-65-5) → Cp(η6-Ph6C6)Cr + 1,5-Hexadien (592-42-7)

Conditions	Yield
In pentane under Ar, addn. of the acetylene to a suspension of the Cr complex in pentane at -78°C, stirred and allowed to warm to 0°C over 7 h , held for 48 h; filtration, cooled to -78°C, crystn., elem. anal., the diene detn. by GC analysis;	A 88.3% B 65.2%

allyl bromide (106-95-6) → 1,5-Hexadien (592-42-7)

Conditions	Yield
With copper acetylacetonate; tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis; 2 F/mol;;	88%
With copper acetylacetonate; tetraethylammonium perchlorate In N,N-dimethyl-formamide Product distribution; other electrolytic conditions, reagents; other allyl halides;	88 % Chromat.
With magnesium In diethyl ether for 0.1h; Product distribution; yield of Wurtz reaction product as a function of the nature of trhe halide and experimental conditions;	10 g

allyl phenyl selenide (14370-82-2) → 1,5-Hexadien (592-42-7) + diphenyl diselenide (1666-13-3)

Conditions	Yield
at 600℃; under 20 Torr; for 0.0333333h;	A 67% B 88%

(allylsulfonyl)benzene (16212-05-8) + allylmagnesium bromide (1730-25-2) → 1,5-Hexadien (592-42-7)

Conditions	Yield
With triphenylphosphine; copper dichloride In tetrahydrofuran at 60℃;	87%

Cp(η3-C3H5)2Cr + acetylene (74-86-2) → Cp(η6-C6H6)Cr + 1,5-Hexadien (592-42-7)

Conditions	Yield
In pentane under Ar, react. vessel with suspension of the Cr complex in pentane at -78°C connected with a gas burette filled with acetylene, warmed slowly to 0.degree,C, stirred for 48 h under absorption of acetylene, brown suspension; filtration, cooled to -78°C, crystn., elem. anal., the diene detn. by GC analysis;	A 86.2% B 85%

benzylidene phenylamine (538-51-2) + allyl bromide (106-95-6) → 1,5-Hexadien (592-42-7) + phenyl-(1-phenyl-but-3-enyl)-amine (66489-79-0)

Conditions	Yield
With tetrabutylammomium bromide; indium(III) chloride In tetrahydrofuran chemo-electrochemical allylation;	A n/a B 86%

[(C5H5)V(C3H5)2] + carbon monoxide (201230-82-2) → tetracarbonyl(η(5)-cyclopentadienyl)vanadium(I) + 1,5-Hexadien (592-42-7)

Conditions	Yield
In tetrahydrofuran reaction of CO with CpV(C3H5)2 in THF (Ar); formation of 1,5-hexadiene in the condensate of the reaction soln., subliming the reaction residue in a high vacuum at 80°C to give CpV(CO)4;	A 86% B 75%

cis-{(PhCH2)2Co(III)(2,2'-bipyridine)2}ClO4 + allyl bromide (106-95-6) → (Co(bpy)2Br)(1+) (747369-48-8) + 1,5-Hexadien (592-42-7) + 4-Phenyl-1-butene (768-56-9) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7)

Conditions	Yield
In [D3]acetonitrile Kinetics; Irradiation (UV/VIS); Degasses condition, 298 K, 11 h;; detected by NMR-spectroscopy;;	A n/a B 36% C 34% D 85%

cis-{(PhCH2)2Co(bpy)2}(1+) + allyl bromide (106-95-6) → (Co(bpy)2Br)(1+) (747369-48-8) + 1,5-Hexadien (592-42-7) + 4-Phenyl-1-butene (768-56-9) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7)

Conditions	Yield
In [D3]acetonitrile Kinetics; Irradiation (UV/VIS); Degasses condition, 298 K, 11 h;; detected by NMR-spectroscopy;;	A n/a B 36% C 34% D 85%

Cp(η3-C3H5)2Cr + buta-1,3-diene (106-99-0) → (CpCr)2(μ-η3,η3-C8H12) + 1,5-Hexadien (592-42-7)

Conditions	Yield
In diethyl ether under Ar, soln. of the Cr complex in diethyl ether treated with a 10-fold excess of butadiene at -30°C, warmed to -5°C over 12 h; evapn., extn. of the residue (pentane), cooling to -78°C, crystn., elem. anal., detn. of the diene by GC analysis;	A 72% B 83%

2-(bromomethyl)acrylic acid (72707-66-5) + allyl bromide (106-95-6) → 1,5-Hexadien (592-42-7) + 2-methylene-5-hexenoic acid (73505-05-2)

Conditions	Yield
With manganese; copper dichloride In tetrahydrofuran; water for 16h; Ambient temperature; Yield given;	A n/a B 79%
With manganese; copper dichloride In tetrahydrofuran; water for 16h; Ambient temperature; Yields of byproduct given;	A n/a B 79%

Cp(η3-C3H5)2Cr + hex-3-yne (928-49-4) → Cp(η6-Et6C6)Cr + 1,5-Hexadien (592-42-7)

Conditions	Yield
In pentane under Ar, addn. of the hexyne to a suspension of the Cr complex in pentane at -78°C, stirred and allowed to warm to 0°C over 7 h , held for 48 h; filtration, cooled to -78°C, crystn., elem. anal., the diene detn. by GC analysis;	A 77.9% B 40%

allyl bromide (106-95-6) + p-methoxybenzylidene-phenylamine (836-41-9) → 1,5-Hexadien (592-42-7) + N-(1-(4-methoxyphenyl)but-3-enyl)benzenamine

Conditions	Yield
With tetrabutylammomium bromide; indium(III) chloride In tetrahydrofuran chemo-electrochemical allylation;	A n/a B 76%

(η5-t-C4H9C5H4)(η3-C3H5)2Cr + acetylene (74-86-2) → (η5-t-C4H9C5H4)(η6-C6H6)Cr + 1,5-Hexadien (592-42-7)

Conditions	Yield
In diethyl ether under Ar, react. of the Cr complex with acetylene saturated diethyl ether at -78°C, stirred and allowed to warm to 0°C over 7 h , held for 48 h; filtration, cooled to -78°C, crystn., elem. anal., the diene detn. by GC analysis;	A 60% B 75%

1 ,6-dibromohexane (629-03-8) → 1-hexene (592-41-6) + hexane (110-54-3) + 1,5-Hexadien (592-42-7) + hexan-1-ol (111-27-3)

Conditions	Yield
With tetramethylammonium perchlorate In 2,2,2-trifluoroethanol; N,N-dimethyl-formamide Electrolysis;	A 4% B 75% C 5% D 18%

Pd(η1-C3H5)(η3-C3H5)(TCNE) + triphenylphosphine (603-35-0) → [(PPh3)2Pd*tetracyanoethylene] (17764-64-6) + 1,5-Hexadien (592-42-7)

Conditions	Yield
In dichloromethane 0°C, then 8 h room temp.; progress of reaction studied by (1)H- and (31)P-NMR; recryst. from CH2Cl2 pentane, dried in vacuo, elem. anal.;	A 71.9% B n/a

Cp(η3-C3H5)2Cr → ((C5H5)CrI2)2 + 1,5-Hexadien (592-42-7)

Conditions	Yield
With I2 In diethyl ether; pentane under Ar, suspension of the Cr complex in pentane at -78°C, addn. of I2 in diethylether, warming up to 0°C, stirring overnight, liberation of hexadiene, pptn. of the product Cr complex; elem. anal., GC detn. of product gas;	A 71.3% B 33%

(allylsulfonyl)benzene (16212-05-8) + allylmagnesium iodide (18854-63-2) → 1,5-Hexadien (592-42-7)

Conditions	Yield
With triphenylphosphine; copper dichloride In tetrahydrofuran at 60℃;	70%

1,5-Hexadien (592-42-7) + triphenylmethylacetonitrile oxide (13412-55-0) → 5-(3-Butenyl)-3-(triphenylmethyl)-2-isoxazoline (111379-53-4)

Conditions	Yield
In benzene for 48h; Heating;	100%
In benzene at 25℃; Yield given;

1,5-Hexadien (592-42-7) + phenylsilane (694-53-1) → [(phenylsilyl)methyl]cyclopentane

Conditions	Yield
With <(CH3)5>2YCH3*THF In cyclohexane for 1h; Mechanism; Ambient temperature; other dienes; other silanes;	100%
With (C5Me5)2YCH3*THF In cyclohexane for 1h; Ambient temperature;	100%
With <(CpTMS)2YMe>2 In cyclohexane for 4h; Ambient temperature;	98%

1,5-Hexadien (592-42-7) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 9,9'-hexane-1,6-diyl-bis-9-bora-bicyclo[3.3.1]nonane (88703-69-9)

Conditions	Yield
In tetrahydrofuran at 40℃; for 24h; Schlenk technique; Inert atmosphere;	100%
In tetrahydrofuran at 20℃; for 3h; Addition;
In tetrahydrofuran at 20℃; for 4.5h; Addition; Hydroboration;
In tetrahydrofuran at 20℃; for 3h;

1,5-Hexadien (592-42-7) → 5-chloro-6-(pentafluoro-λ6-sulfanyl)hex-1-ene (860438-41-1)

Conditions	Yield
With pentafluorosulfanyl chloride; triethyl borane In hexane at -30 - 20℃;	100%

1,5-Hexadien (592-42-7) + [Y(η5:η1-C5Me4SiMe2NCMe3)(THF)(μ-H)]2 → [Y(η5:η1-C5Me4SiMe2NCMe3)(CH2CH(CH2)4)(THF)]

Conditions	Yield
In benzene-d6 reaction in NMR tube, at room temp., for 3 h; solvent was removed in vac.; NMR;	100%

1,5-Hexadien (592-42-7) → 1,5-hexadiene diepoxide (1888-89-7, 74892-51-6, 74892-53-8, 131722-62-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16h;	99%
With 3-chloro-benzenecarboperoxoic acid at 10 - 20℃; for 19h;	95.1%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane	87%

1,5-Hexadien (592-42-7) → 3-methyl-cyclopentanone (1757-42-2, 6195-92-2)

Conditions	Yield
With Pd(II)(15-crown-5-phen)Cl2; dinitrogen monoxide In N,N-dimethyl acetamide; water at 150℃; under 2250.23 Torr; for 18h;	99%

1,5-Hexadien (592-42-7) + p-methoxyphenylbutadiene (30448-78-3) → 1,1'-[(2Z,10Z)-5,8-bis(methylene)dodeca-2,10-diene-1,12-diyl]bis(4-methoxybenzene) (1175163-69-5)

Conditions	Yield
With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane at 20℃; Inert atmosphere;	99%

1,5-Hexadien (592-42-7) → (2E,4E)-hexa-2,4-diene (5194-51-4)

Conditions	Yield
With Polystyrene-supported 4-tert-butyl-2-(diisopropylphosphino)-1H-imidazole and ruthenium complex In [(2)H6]acetone at 70℃; for 7h; Reagent/catalyst; Inert atmosphere; Glovebox; stereoselective reaction;	98%
With tris(η3-allyl)chromium In n-heptane at 59.9℃; Rate constant; Equilibrium constant;

1,5-Hexadien (592-42-7) → (2R,5RS)-1,2,5,6-hexanetetrol

Conditions	Yield
With potassium carbonate; potassium hexacyanoferrate(III); potassium osmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 0 - 6℃; for 29h; Sharpless dihydroxylation;	98%

1,5-Hexadien (592-42-7) + pyridazine-4,5-dicarbonitrile (17412-15-6) → 8,9-dicyanotricyclo[4.3.1.03,7]dec-8-ene

Conditions	Yield
In chloroform at 110℃; Diels-Alder reaction;	98%

2-tert-butylpyridine (5944-41-2) + 1,5-Hexadien (592-42-7) → C15H23N

Conditions	Yield
With tris(pentafluorophenyl)borate; C42H51N3PSc In chlorobenzene at 100℃; for 5h; diastereoselective reaction;	98%

1,5-Hexadien (592-42-7) + Phenetole (103-73-1) → C14H20O

Conditions	Yield
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 70℃; for 3h; stereoselective reaction;	98%

1,5-Hexadien (592-42-7) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) → 1,1,1,2,2,3,3,4,4,11,11,12,12,13,13,14,14,14-octadecafluoro-6,9-diiodotetradecane (40735-23-7)

Conditions	Yield
With sodiumsulfide nonahydrate; dibenzoyl peroxide at 80℃; for 4h;	97.1%
With 2,2'-azobis(isobutyronitrile)

1,5-Hexadien (592-42-7) → 2,5-diiodomethyltetrahydrofuran (134692-33-4)

Conditions	Yield
With iodine; sodium hydrogencarbonate In tetrahydrofuran; diethyl ether; water at 20℃; for 4h;	97%
With iodine; sodium hydrogencarbonate In tetrahydrofuran; water Inert atmosphere;

3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine (16453-18-2) + 1,5-Hexadien (592-42-7) → 4-(but-3'-enyl)-1,4-dihydro-3,6-bis(trifluoromethyl)-pyridazine

Conditions	Yield
In dichloromethane Ambient temperature;	97%

1,5-Hexadien (592-42-7) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → 2,3,10,11-tetramethyl-5,8-dimethylene-2,10-dodecadiene

Conditions	Yield
With tetrabutylammonium borohydride; zinc(II) iodide; cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane] In dichloromethane at 25℃; for 16h;	97%
With tetrabutylammonium borohydride; zinc(II) iodide; cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane] In dichloromethane at 20℃; for 20h;	97%
With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane for 20h;	57%

silver tetrafluoroborate (14104-20-2) + chlorobis(cyclooctene)rhodium(I) dimer + 1,5-Hexadien (592-42-7) → [Rh(4,4'-dimethyl-2,2'-bipyridine)(hexadiene)]BF4 (471254-42-9)

Conditions	Yield
In methanol; dichloromethane under N2, excess of diene was added to MeOH suspn. of Rh-complex, stirring at room temp. for 1.5 h, 2 equiv. of N-base was added in CH2Cl2, stirring at room temp. for 1 h, 2 equiv. of AgBF4 was added dropwise in CH2Cl2, stirring at room temp. for 1 h; soln. was filtered, concd., Et2O was added, solid was filtered off, washed with Et2O, dried in vac., elem. anal.;	97%

silver(I) hexafluorophosphate (26042-63-7) + (2-methylallyl)palladium-chloride dimer + 1,5-Hexadien (592-42-7) → η(4)-hexa-1,5-diene(η(3)-2-methylallyl)palladium hexafluorophosphate

Conditions	Yield
In dichloromethane N2-atmosphere; elem. anal.;	97%

4-chIoro-2-methylpyridine (3678-63-5) + 1,5-Hexadien (592-42-7) → C12H16ClN

Conditions	Yield
With tris(pentafluorophenyl)borate; C42H51N3PSc In chlorobenzene at 100℃; for 12h; diastereoselective reaction;	97%

1,5-Hexadien (592-42-7) + 1-(tert-butyl)-4-methoxybenzene (5396-38-3) → C17H26O

Conditions	Yield
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 70℃; for 1.5h; stereoselective reaction;	97%

1,5-Hexadien (592-42-7) + 4-chloromethoxybenzene (623-12-1) → C13H17ClO

Conditions	Yield
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 70℃; for 2h; stereoselective reaction;	97%

3-methoxyphenyl bromide (2398-37-0) + 1,5-Hexadien (592-42-7) → C13H17BrO

Conditions	Yield
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 70℃; for 6h; stereoselective reaction;	97%

1,5-Hexadien (592-42-7) + N-methyl-N-ethylaniline (613-97-8) → C15H23N

Conditions	Yield
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 50℃; for 2h; stereoselective reaction;	97%

N-methyl-1,2,3,4-tetrahydroquinoline (491-34-9) + 1,5-Hexadien (592-42-7) → C16H23N

Conditions	Yield
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 50℃; for 23h; stereoselective reaction;	97%

1,5-Hexadien (592-42-7) + 3-bromo-2-picoline (38749-79-0) → C12H16BrN

Conditions	Yield
With C42H51N3PSc; trityl tetrakis(pentafluorophenyl)borate In chlorobenzene at 100℃; for 5h; diastereoselective reaction;	96%

1,5-Hexadien (592-42-7) + 4-methoxylbiphenyl (613-37-6) → C19H22O

Conditions	Yield
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 70℃; for 1h; stereoselective reaction;	96%

1-bromo-4-methoxy-benzene (104-92-7) + 1,5-Hexadien (592-42-7) → C13H17BrO

Conditions	Yield
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 70℃; for 4h; stereoselective reaction;	96%

Upstream product

• 187737-37-7 propene 
• 1981-80-2 allyl radical 
• 544-01-4 isopentyl ether 
• 855473-89-1 1-mesityl-2,2-dimethyl-pent-4-en-1-one 
• 110-54-3 hexane 
• 96-11-7 1,2,3-tribromopropane 
• 557-40-4 Allyl ether 
• 6222-17-9 1,6-diacetoxyhexane 
• 106-95-6 allyl bromide 
• 60-29-7 diethyl ether 
• 925-90-6 ethylmagnesium bromide 
• 107-05-1 3-chloroprop-1-ene 
• 28276-08-6 1,1-dimethylpropylmagnesium chloride 
• 591-87-7 Allyl acetate 

Downstream Products

• 51287-99-1 1,1,1,3-tetrachloro-7-heptene 
• 61856-19-7 1,1,1,3,6,8,8,8-octachlorooctane 
• 10353-53-4 1,2-epoxy-5-hexene 
• 1888-89-7 1,5-hexadiene diepoxide 
• 7736-35-8 (3-butenyl)cyclopropane 
• 37520-11-9 1,2-Dicyclopropyl-aethan 
• 2678-29-7 1,6-bis-acetylsulfanyl-hexane 
• 1003-38-9 2,5-dimethyltetrahydrofuran 
• 104-80-3 tetrahydrofuran-2,5-dimethanol 
• 592-41-6 1-hexene 
• 629-03-8 1 ,6-dibromohexane 
• 821-41-0 5-Hexen-1-ol 
• 629-11-8 1,6-hexanediol 
• 187737-37-7 propene 

Relevant articles and documents

Mechanism of the Cope Rearrangement of Acyclic 1,5-Dienes and of the Wacker Oxidation of Alk-1-enes catalysed by Palladium Complexes

Hexa-1,5-diene is catalytically converted into acetone in an aqueous solution of (PhCN)2PdCl2, CuCl2, and CuCl at 60 deg C in the presence of oxygen, thereby revealing a hitherto unsuspected role of η3-allylic intermediates in both the PdII-catalysed Cope rearrangements of 1,5-dienes and the selective Wacker oxidation of propene and higher alk-1-enes to ketones.

Extrinsic precursor-assisted synthesis of 1,5-hexadiene on Cu(100)

The reaction between allyl bromide and previously chemisorbed η3-allyl to form 1,5-hexadiene on Cu(100) at cryogenic temperatures has been examined using reflection absorption infrared spectroscopy and temperature-programmed desorption. Above 110 K, the 1,5-hexadiene formation rate decreases with increasing temperature and is controlled by the residence time of dosed allyl bromide, whereas below 100 K, the rate increases with temperature and is controlled by the reaction of weakly adsorbed allyl bromide with chemisorbed η3-allyl. Above 110 K, a precursor state model is used to interpret the data. The activation energy difference, Ed-Er, between desorption and reaction of allyl bromide with η3-allyl is 12 kJ mol-1.

Reaktion von (1,4-Diazabutadien)bis(alken)nickel(0)-Komplexen mit Ethin

The (1,4-diazabutadiene)bis(alkene)nickel(0) complexes iPr2Ph)2-dad>Ni(C2H4)2 iPr2Ph)2-dad = 2,6iPr2C6H3-N=CHCH=N-C6H3-2,6iPr2> (1) and iPr2Ph)2-dad>Ni(η2,η2-C6H10) (2) react with ethyne above - 100 deg C (1) or -30 deg C (2) with coupling of two ethyne molecules to afford the dinuclear complex iPr2Ph)2-dad>Ni>2(C4H4) (3) which contains a ferrol-type nickelacyclopentadiene-nickel(O) bonding element.A single-crystal X-ray structure study of 3 revealed strongly distorted coordination geometries of the nickel centers, which are also present in solution at low temperature (1H, 13C-NMR).At higher temperatures dynamic processes take place by which the coordinative distortions at the nickel centers are reversed and the bonding situations of the nickel atoms are exchanged.However, a rotation of the phenyl groups around the N-C bonds can be excluded.Similarly, Ni>2(C4H4) (4) has been obtained and characterized.

Kinetics and Mechanism of Thermal Decomposition of Bis(Η3-Allyl)Nickel Complexes

Abstract: The kinetics of thermal decomposition of bis(η3-allyl) nickel complexes in various media is studied. The specific features of the mechanism are determined, including the combination of the stages of trans-cis isomerization of Niall2 and the bimolecular decomposition of the cis-isomer with diallyl formation. The effect of autocatalytic decomposition of complexes with metallic nickel is been detected. The qualitative dependences of the process rate on the nature of the solvent and the structure of the allyl ligand are determined. The activation parameters of individual steps, consistent with quantum chemical calculations, are found.

Method for preparing 1, 5-hexadiene

The invention discloses a method for preparing 1, 5-hexadiene, which is characterized in that under the action of a catalyst and a reducing agent, a substrate is catalyzed to be subjected to a one-step reaction to prepare the 1, 5-hexadiene, and the substrate comprises a polyhydroxy compound and a derivative thereof. Therefore, the invention provides a novel method for synthesizing the 1, 5-hexadiene. According to the reaction path provided by the invention, new application of catalytic conversion of polyhydroxy compounds including glycerol is developed through a carbon chain extension conversion strategy.

Reductive C(sp3)-C(sp3) homo-coupling of benzyl or allyl halides with H2using a water-soluble electron storage catalyst

This paper reports the first example of a reductive C(sp3)-C(sp3) homo-coupling of benzyl/allyl halides in aqueous solution by using H2as an electron source {turnover numbers (TONs) = 0.5-2.3 for 12 h}. This homo-coupling reaction, promoted by visible light, is catalysed by a water-soluble electron storage catalyst (ESC). The reaction mechanism, and four requirements to make it possible, are also described.

Mild olefin formationviabio-inspired vitamin B12photocatalysis

Dehydrohalogenation, or elimination of hydrogen-halide equivalents, remains one of the simplest methods for the installation of the biologically-important olefin functionality. However, this transformation often requires harsh, strongly-basic conditions, rare noble metals, or both, limiting its applicability in the synthesis of complex molecules. Nature has pursued a complementary approach in the novel vitamin B12-dependent photoreceptor CarH, where photolysis of a cobalt-carbon bond leads to selective olefin formation under mild, physiologically-relevant conditions. Herein we report a light-driven B12-based catalytic system that leverages this reactivity to convert alkyl electrophiles to olefins under incredibly mild conditions using only earth abundant elements. Further, this process exhibits a high level of regioselectivity, producing terminal olefins in moderate to excellent yield and exceptional selectivity. Finally, we are able to access a hitherto-unknown transformation, remote elimination, using two cobalt catalysts in tandem to produce subterminal olefins with excellent regioselectivity. Together, we show vitamin B12to be a powerful platform for developing mild olefin-forming reactions.

Method for preparing 2, 5-hexanedione

The invention discloses a method for preparing 2, 5-hexanedione, which is characterized in that a polyhydroxy compound and a derivative thereof are used as substrates, and the 2, 5-hexanedione is obtained through a carbon growth-wacker oxidation reaction under the action of a catalyst and an oxidizing agent. According to the method disclosed by the invention, a large amount of by-product glycerol generated in a biodiesel production process is used as a raw material, so that the production cost of 2, 5-hexanedione can be reduced, and a high-added-value conversion and utilization path is provided for glycerol.

The Synthesis of Chiral Allyl Carbamates via Merger of Photoredox and Nickel Catalysis

A mild, and versatile, organophotoredox/Ni-mediated protocol was developed for the direct preparation of diverse, enantioenriched allyl carbamates. The reported approach represents a significant departure from classical step-by-step synthesis of allyl carbamates. This dual photoredox/Ni based strategy offers unrivalled capacity for convergent unification of readily available alkyl halides and chiral carbamates derived from 1-bromo-alken-3-ols with high chemoselectivity and efficiency. The reported photoredox/Ni catalyzed cross-coupling reaction is not limited to carbamates, but also to other O-derivatives such as esters, ethers, acetals, carbonates or silyl ethers. To demonstrate the utility of the reported protocol, the resulting allyl carbamates were transformed into functionalized non-racemic allylamines through a sigmatropic rearrangement reaction in enantiospecific manner. This approach allowed for synthesis of enantiomeric allylamines by a simple control of the geometry of a double bond of allyl carbamates. (Figure presented.).

Chlorinating preparation method for low-carbon olefins

The invention discloses a chlorinating preparation method for low-carbon olefins. According to the method, chlorine gas is diluted with inert gas and then reacts with low-carbon olefins, thus, influence caused by microscopic mixing can be obviously reduced, namely, a too high local temperature can be avoided, thus, side reactions including a decarbonization phenomenon caused by the too high localtemperature can be obviously reduced, and a relatively good chloride yield can be obtained.