2004-70-8

Basic information

• Product Name: 1,3-Pentadiene, (3E)-
• Synonyms: 1,3-Pentadiene,(E)- (8CI); Piperylene, trans- (6CI); (3E)-1,3-Pentadiene; (E)-1,3-Pentadiene;(E)-Piperylene; 1,3-trans-Pentadiene; NSC 73901; trans-1,3-Pentadiene;trans-1-Methyl-1,3-butadiene; trans-1-Methylbutadiene; trans-Piperylene
• CAS NO: 2004-70-8
• Molecular Formula: C₅H₈
• Molecular Weight: 68.117
• EINECS: 217-909-5
• Mol File: 2004-70-8.mol
• Article Data: 77

Chemical Properties

• Melting Point: 87 °C(lit.)
• Boiling Point: 42 °C(lit.)
• Flash Point: °C
• Appearance: /
• Density: 0.683 g/mL at 25 °C(lit.)
• Vapor Density: 2.4 (vs air)
• Vapor Pressure: 380mmHg at 25°C
• Refractive Index: 1.415
• Storage Temp.: Refrigerator
• Stability: Stable. Highly flammable. Readily forms explosive mixtures with air. Note low flash point. Incompatible with strong oxidizing agents.
• BRN: 1523659
• CAS DataBase Reference: 1,3-Pentadiene, (3E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Pentadiene, (3E)-(2004-70-8)
• EPA Substance Registry System: 1,3-Pentadiene, (3E)-(2004-70-8)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-65-36/37/38
• Safety Statements: 16-23-26-36-62
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• RTECS: RZ2465000
• HazardClass: 3.1
• PackingGroup: I
• Hazardous Substances Data: 2004-70-8(Hazardous Substances Data)

Usage

Definition

ChEBI: An alkadiene consisting of pentane with the two double bonds located at positions 1 and 3.

General Description

Trans-1,3-Pentadiene spectra is recorded in the 5000-17500 cm(-1) region with conventional and intracavity laser photoacoustic spectroscopy. It can be determined by the spectrophotometric method based on the Diels-Alder reaction. In this reaction, cisoid 1,3-dienes and tetracyanoethylene (TCNE) react with an aromatic-TCNE pi-complex.

Safety Profile

Poison by intravenous route. A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+

Synthetic route

2-iodo-4-pentene (59967-14-5) → 1-methylbuta-1,3-diene (2004-70-8)

Conditions	Yield
With silver(I) acetate In benzene at 25℃; for 18h;	89%

4,5-epithia-2-pentene (202803-83-6) → 1-methylbuta-1,3-diene (2004-70-8) + 3,6-dihydro-3-methyl-1,2-dithiin

Conditions	Yield
With pentacarbonyl(acetonitrile)tungsten In dichloromethane-d2 at 25℃; for 24h;	A n/a B 86%
With pentacarbonyl(acetonitrile)tungsten In dichloromethane-d2 for 24h; Ambient temperature;	A n/a B 86 % Spectr.

(1S,3S,7R)-3-Methyl-4-thia-tricyclo[5.2.1.02,6]dec-8-ene 4,4-dioxide (83927-50-8, 88979-80-0) → 1-methylbuta-1,3-diene (2004-70-8) + cyclopenta-1,3-diene (542-92-7)

Conditions	Yield
at 650℃; under 0.01 Torr; Title compound not separated from byproducts;	A 85% B n/a
at 650℃; Yields of byproduct given;

4,5-epithia-2-pentene (202803-83-6) → 1-methylbuta-1,3-diene (2004-70-8)

Conditions	Yield
Heating;	54%
With triphenylphosphine	54%

1,4-dioxane (123-91-1) + 2-chloro-but-2-ene (4461-41-0) → 1-methylbuta-1,3-diene (2004-70-8) + 4,5-dimethyl-2,6-octadiene (18476-57-8) + 1-methyl-2-butenylaluminum sesquichloride

Conditions	Yield
With aluminium at 100 - 110℃; for 6h; Product distribution; ultrasonic bath;	A 15% B 50% C 18%

bis(2,4-pentadienyl)magnesium THF complex → Z-piperylene (1574-41-0) + 1-methylbuta-1,3-diene (2004-70-8) + 1,4-Pentadiene (591-93-5)

Conditions	Yield
With acetic acid In benzene at 10℃; Product distribution; other protonolysis agents, other bis(dienyl)magnesium complex;	A 8% B 48% C 44%

trans-Crotonaldehyde (123-73-9) + Methyltriphenylphosphonium bromide (1779-49-3) → 1-methylbuta-1,3-diene (2004-70-8)

Conditions	Yield
With n-butyllithium In 1,4-dioxane; toluene at 20℃; Inert atmosphere;	39%

(π-CH3CHCHCHCH3NiCl)2 → 1-methylbuta-1,3-diene (2004-70-8) + decane (124-18-5) + 2-pentene (109-68-2)

Conditions	Yield
In toluene 140°C;	A 10% B 20% C 30%

isobutene (115-11-7) → 1-butylene (106-98-9) + (Z)-2-Butene (590-18-1) + 2-methyl-but-2-ene (513-35-9) + Z-piperylene (1574-41-0) + 1-methylbuta-1,3-diene (2004-70-8) + propene (187737-37-7) + methane (34557-54-5) + trans-2-Butene (624-64-6) + (Z)-pent-2-ene (627-20-3) + (E)-pent-2-ene (646-04-8) + ethane (74-84-0) + propane (74-98-6) + Isobutane (75-28-5) + methylbutane (78-78-4) + ethene (74-85-1) + 1-penten (109-67-1) + Cyclopentane (287-92-3) + 2-Methyl-1-butene (563-46-2) + 3-Methyl-1-butene (563-45-1) + cyclopentene (142-29-0) + n-butane (106-97-8) + pentane (109-66-0)

Conditions	Yield
CBV1502 at 579.84℃; under 900.09 Torr; Product distribution / selectivity;	A 2.6% B 2.4% C 1.29% D 0.05% E 0.03% F 24.95% G 0.73% H 3.19% I 0.32% J 0.58% K 0.36% L 2.08% M 2.15% N 0.34% O 9.61% P 0.23% Q 0.4% R 0.71% S 0.14% T 0.14% U 1.8% V 0.16%
CBV28014 at 509.84℃; under 900.09 Torr; Product distribution / selectivity;	A 6.71% B 7.3% C 5.62% D 0.02% E 0.03% F 23.29% G 0.09% H 9.97% I 1.1% J 2.06% K 0.07% L 1.24% M 1.95% N 0.59% O 3.25% P 0.7% Q 0.31% R 2.72% S 0.47% T 0.21% U 1.37% V 0.26%

...Expand

1,4-Pentadiene (591-93-5) → 1-methylbuta-1,3-diene (2004-70-8) + ethenylcyclopropane (693-86-7) + cyclopenta-1,3-diene (542-92-7) + buta-1,3-diene (106-99-0) + cyclopentene (142-29-0)

Conditions	Yield
Product distribution; Mechanism; Plasmolysis (40 W, 3.48mmol/min, 13.56 MHz);	A n/a B 5% C 21% D n/a E 18%

Z-piperylene (1574-41-0) → 1-methylbuta-1,3-diene (2004-70-8)

Conditions	Yield
silver trifluoromethanesulfonate In acetonitrile for 2h; Irradiation;	18.4%
In acetonitrile for 1h; Quantum yield; Product distribution; Irradiation; different reaction times;
In benzene Quantum yield; Irradiation; 1-isopropylanthrone as photosensitizer;

(π-CH3CHCHCHCH3NiCl)2 + 2,3,5,6-tetrafluoro-1,4-benzoquinone (527-21-9) → 1-methylbuta-1,3-diene (2004-70-8) + dipentenyl

Conditions	Yield
In toluene molar ratio (CH3CHCHCHCH3NiCl)2:tetrafluoro-p-benzoquinone 1:1, 20°C;	A 13% B 4%

(π-CH3CHCHCHCH3NiCl)2 + chloranil (118-75-2) → 1-methylbuta-1,3-diene (2004-70-8) + dipentenyl

Conditions	Yield
In toluene molar ratio (CH3CHCHCHCH3NiCl)2:tetrachloro-p-benzoquinone 1:1, 20°C;	A 13% B 1%
In toluene molar ratio (CH3CHCHCHCH3NiCl)2:tetrachloro-p-benzoquinone 1:1, 10°C;	A 10-12 B 5-6
In toluene molar ratio (CH3CHCHCHCH3NiCl)2:tetrachloro-p-benzoquinone 1:1, 50°C;	A 19-24 B 3-4

Z-piperylene (1574-41-0) → 3-buten-1-yne (689-97-4) + 1-methylbuta-1,3-diene (2004-70-8) + 4-methyl-2-pentene (4461-48-7) + cyclopenta-1,3-diene (542-92-7) + buta-1,3-diene (106-99-0) + acetylene (74-86-2)

Conditions	Yield
at 20℃; under 0.4 Torr; Product distribution; Irradiation; variation of pressure and additives;	A 0.2% B 0.3% C 0.13% D 0.25% E 0.09% F 0.22%

2-ethoxy-ethanol (110-80-5) + (±)-(1-chloroethyl)cyclopropane (10524-06-8) → 1-methylbuta-1,3-diene (2004-70-8) + ethenylcyclopropane (693-86-7)

Conditions	Yield
With potassium hydroxide Siedetemperatur;

2,4-diacetoxy-pentane (7371-86-0) → Z-piperylene (1574-41-0) + 1-methylbuta-1,3-diene (2004-70-8) + 1,4-Pentadiene (591-93-5)

Conditions	Yield
at 575 - 600℃;

(+/-)-trimethyl-(1-methyl-but-2t-enyl)-ammonium; trimethyl-(1-methyl-but-2t-enyl)-ammonium hydroxide → Z-piperylene (1574-41-0) + 1-methylbuta-1,3-diene (2004-70-8)

Conditions	Yield
at 160℃;

cyclopentene (142-29-0) → 1-methylbuta-1,3-diene (2004-70-8) + 1-Pentyne (627-19-0)

Conditions	Yield
at 1227℃; Equilibrium constant;

3-buten-1-yne (689-97-4) + (Z)-azomethane (4143-42-4) → Z-piperylene (1574-41-0) + 1-methylbuta-1,3-diene (2004-70-8) + 1-Pentyne (627-19-0) + 3-methyl-1-pentyne (922-59-8) + (Z)-3-methyl-1,3-pentadiene (2787-45-3)

Conditions	Yield
In gas at 299.9℃; Thermodynamic data; Rate constant; Kinetics; Heating; other temperature;

penta-1,3-diene (504-60-9) → Z-piperylene (1574-41-0) + 1-methylbuta-1,3-diene (2004-70-8) + (Z)-pent-2-ene (627-20-3) + (E)-pent-2-ene (646-04-8) + 1-penten (109-67-1) + pentane (109-66-0)

Conditions	Yield
With hydrogen; rhenium In methanol at 100℃; under 18751.5 Torr; for 4h; Product distribution; various rhenium complexes with cyclic sulfides as catalysts of hydrogenation and isomeization of olefins;

Z-piperylene (1574-41-0) + 3-bromobicyclo<3.2.1>oct-2-en-7-one (81095-66-1) → 1-methylbuta-1,3-diene (2004-70-8) + 1-bromotricyclo<3.2.1.02,7>octan-3-one (81095-74-1) + 1-bromobicyclo<3.2.1>oct-2-en-7-one (81095-71-8)

Conditions	Yield
With acetophenone In benzene Product distribution; Mechanism; Irradiation; cis-piperylene concentration dependence, other solvent;

Z-piperylene (1574-41-0) → 1-methylbuta-1,3-diene (2004-70-8) + (Z)-pent-2-ene (627-20-3) + (E)-pent-2-ene (646-04-8) + 1-penten (109-67-1) + pentane (109-66-0)

Conditions	Yield
With hydrogen at 49.9℃; Mechanism; effect of different MoO3/Al2O3 catalysts;

propene (187737-37-7) → 1-butylene (106-98-9) + 1-methylbuta-1,3-diene (2004-70-8) + butene-2 (107-01-7) + ethene (74-85-1) + buta-1,3-diene (106-99-0) + isobutene (115-11-7)

Conditions	Yield
at 518.9℃; under 100 Torr; Product distribution; Rate constant; Mechanism; thermal reaction of propene, effect of the walls of the reactor;

1,4-Pentadiene (591-93-5) → 1-methylbuta-1,3-diene (2004-70-8)

Conditions	Yield
With potassium salt of 1,3-diaminopropane In dimethyl sulfoxide at 5℃; Thermodynamic data; other solvent: cyclohexylamine, other temperature: 15 degC; ΔH(isomer.);

1,4-Pentadiene (591-93-5) → Z-piperylene (1574-41-0) + 1-methylbuta-1,3-diene (2004-70-8) + cyclopenta-1,3-diene (542-92-7)

Conditions	Yield
Ambient temperature; Irradiation;
Product distribution; Ambient temperature; Irradiation; investigated effect of argon buffer gas and fluence dependence;

1,4-Pentadiene (591-93-5) → Z-piperylene (1574-41-0) + 1-methylbuta-1,3-diene (2004-70-8) + isoprene (78-79-5)

Conditions	Yield
DpSc-H at 140℃; Product distribution;

(Z)-pent-2-ene (627-20-3) → Z-piperylene (1574-41-0) + 1-methylbuta-1,3-diene (2004-70-8) + methane (34557-54-5) + (E)-pent-2-ene (646-04-8) + ethene (74-85-1) + acetaldehyde (75-07-0)

Conditions	Yield
With (per)acetylperoxyboric acid; hydrogen; oxygen at 480℃; Mechanism;	A 6.0 % Chromat. B 14.7 % Chromat. C 11.0 % Chromat. D 30.5 % Chromat. E 11.0 % Chromat. F 9.8 % Chromat.

cis-3-hexene (7642-09-3) → but-1-yne (107-00-6) + 1-methylbuta-1,3-diene (2004-70-8) + methane (34557-54-5) + ethene (74-85-1) + buta-1,3-diene (106-99-0) + acetylene (74-86-2)

Conditions	Yield
With oxygen under 0.1 - 60 Torr; Quantum yield; Mechanism; Irradiation; effect of pressure on the product distribution , and of the wave length on the product distribution and on fragmentation pattern;

(E)-4-methylpent-2-ene (674-76-0) → 1-methylbuta-1,3-diene (2004-70-8) + buta-1,3-diene (106-99-0) + isoprene (78-79-5)

Conditions	Yield
at 660 - 750℃; Thermodynamic data; Kinetics; Product distribution; cracking, reaction time 0.05 to 1.5 sec.;

1-methylbuta-1,3-diene (2004-70-8) + 2-formyl-4,4-dimethylcyclohexa-2,5-dien-1-one (30758-46-4) → (4aS,5S,8aS)-1,1,5-Trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carbaldehyde (77994-85-5)

Conditions	Yield
In benzene at 70℃;	100%

1-methylbuta-1,3-diene (2004-70-8) → 4-chloro-1-pentafluorosulfanylpent-2-ene

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

1-methylbuta-1,3-diene (2004-70-8) + (π-CD3CDCDCD2NiI)2 → (π-C4D7CHCHCHCH3NiI)2

Conditions	Yield
In benzene educts in stochiometric amt.;	100%

1-methylbuta-1,3-diene (2004-70-8) + (π-CD3CDCDCD2NiI)2 → anti-(C4(2)H7CHCHCH(CH3)NiI)2

Conditions	Yield
in stoihometric amt.;	100%
in stoihometric amt.;	100%

(η6-naphthalene)(η4-1,5-cyclooctadiene)ruthenium(0) (88945-10-2) + 1-methylbuta-1,3-diene (2004-70-8) + trimethylphosphane (594-09-2) → [ruthenium(0)(η4-(E)-cisoid-1,3-pentadiene)(η4-1,5-COD)(PMe3)] (1373229-50-5, 1373244-44-0)

Conditions	Yield
In acetonitrile; benzene byproducts: naphthalene; under N2, Schlenk and vacuum techniques; suspn. of Ru complex (NCCH3) treated with satd. soln. of CH2CHCHCH2CH3 (benzene) at room temp. for 1 h,then treated with PMe3; evapd. to dryness under vac., extracted with hexane, filtered, concd. (vac.), crystd. at cooling for 2 d (dry ice);	100%

(η6-naphthalene)(η4-1,5-cyclooctadiene)ruthenium(0) (88945-10-2) + 1-methylbuta-1,3-diene (2004-70-8) + benzonitrile (100-47-0) → Ru[η(4)-cisoid-(E)-1,3-pentadiene](η(4)-1,5-COD)-(NCMe) (1373229-34-5, 1373244-42-8)

Conditions	Yield
In acetonitrile; benzene byproducts: naphthalene; under N2, Schlenk and vacuum techniques; suspn. of Ru complex (NCCH3) treated with satd. soln. of CH2CHCHCH2CH3 (benzene) at room temp. for 1 h; evapd. to dryness under vac., extracted with hexane, filtered, concd. (vac.), crystd. at cooling for 2 d (dry ice);	100%

1-methylbuta-1,3-diene (2004-70-8) + 7-methyl-1,4-dioxaspiro<4.5>deca-6,9-dien-8-one (75714-50-0) → C14H18O3 (344285-35-4)

Conditions	Yield
With molecular sieve In dichloromethane at 23℃; for 16h; Diels-Alder reaction;	99%

diethyl diazodicarboxylate (4143-61-7) + 1-methylbuta-1,3-diene (2004-70-8) → diethyl 3-methyl-1,2,3,6-tetrahydro-1,2-pyridazincarboxylate (104116-54-3)

Conditions	Yield
With lanthanum(lll) triflate at 20℃; for 0.5h; hetero-Diels-Alder reaction;	99%

N-(4,4-dimethoxy-cyclohexa-2,5-dienylidene)-4-nitro-benzenesulfonamide (697758-88-6) + 1-methylbuta-1,3-diene (2004-70-8) → N-(4-methoxy-8-methyl-5,8-dihydro-naphthalen-1-yl)-4-nitro-benzenesulfonamide

Conditions	Yield
Stage #1: N-(4,4-dimethoxy-cyclohexa-2,5-dienylidene)-4-nitro-benzenesulfonamide; 1-methylbuta-1,3-diene With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 100℃; for 7h; Diels-Alder reaction; Stage #2: With hydrogenchloride In tetrahydrofuran for 0.5h;	99%

1-methylbuta-1,3-diene (2004-70-8) + N,N'-di-tert-butyldiaziridinone (19656-74-7) → 1,3-di-tert-butyl-4-methyl-5-vinyl-imidazolidin-2-one

Conditions	Yield
With copper(I) bromide In chloroform-d1 at 0℃; for 20h; Inert atmosphere; regioselective reaction;	99%
tetrakis(triphenylphosphine) palladium(0) In benzene-d6 at 65℃; for 0.5h;	94%
With sodium tert-pentoxide; N-heterocyclic carbene-Pd(0) complex In tetrahydrofuran at 65℃; for 12h;	94%

1-methylbuta-1,3-diene (2004-70-8) + N,N'-di-tert-butyldiaziridinone (19656-74-7) → C14H26N2O

Conditions	Yield
With copper(I) bromide In chloroform at 0℃; for 20h; Inert atmosphere; regioselective reaction;	99%

1-methylbuta-1,3-diene (2004-70-8) + 2-Formyl-4,4-dimethyl-6-(phenylselenenyl)cyclohexa-2,5-dienone (77630-17-2) → (4aS,5S,8aS)-1,1,5-Trimethyl-4-oxo-3-phenylselanyl-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carbaldehyde (77994-86-6)

Conditions	Yield
In benzene at 70℃;	98%

1-methylbuta-1,3-diene (2004-70-8) + 3,3-dimethyl-6-oxo-cyclohexa-1,4-dienecarbonitrile (123395-80-2) → (4aS,5S,8aS)-1,1,5-Trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carbonitrile

Conditions	Yield
With zinc(II) chloride In diethyl ether at 20℃; for 5h; Cycloaddition; Diels-Alder reaction;	98%

1-methylbuta-1,3-diene (2004-70-8) + aniline (62-53-3) → 2,4,6-tri(1-methylbut-2-en-1-yl)aniline (216437-12-6)

Conditions	Yield
With aluminium trichloride In benzene at 130℃; for 5h;	98%

triphenyl phosphite (101-02-0) + (η6-naphthalene)(η4-1,5-cyclooctadiene)ruthenium(0) (88945-10-2) + 1-methylbuta-1,3-diene (2004-70-8) → [ruthenium(0)(η4-(E)-cisoid-1,3-pentadiene)(η4-1,5-COD)(P(OPh)3)] (1373229-48-1)

Conditions	Yield
In acetonitrile; benzene byproducts: naphthalene; under N2, Schlenk and vacuum techniques; suspn. of Ru complex (NCCH3) treated with satd. soln. of CH2CHCHCH2CH3 (benzene) at room temp. for 1 h,then treated with P(OPh)3; evapd. to dryness under vac., extracted with hexane, filtered, concd. (vac.), crystd. at cooling for 2 d (dry ice);	98%

1-methylbuta-1,3-diene (2004-70-8) + N-(2,4-dichloro-6-oxo-2,4-cyclohexadien-1-ylidene)-4-nitrobenzamide (90388-37-7) → 5,7-dichloro-3,4-dihydro-4-(4-nitrobenzoyl)-2-E-(1-propenyl)-2H-1,4-benzoxazine (118778-81-7)

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	97%

1-methylbuta-1,3-diene (2004-70-8) + [1,4]naphthoquinone (130-15-4) → 1-Methyl-1,4,4a,9a-tetrahydro-anthraquinone (71316-98-8)

Conditions	Yield
	97%

1-methylbuta-1,3-diene (2004-70-8) + methyl 2-acetoxyacrylate (686-46-4) → 4-acetoxy-4-carbomethoxy-3-methylcyclohexene (70291-20-2)

Conditions	Yield
With 2-hydroxyresorcinol at 160℃; for 20h; sealed, evacuated ampule;	97%

1-methylbuta-1,3-diene (2004-70-8) → polypentadiene; monomer(s): trans-1,3-pentadiene

Conditions	Yield
With aluminium trichloride In pentane at 20℃; for 2h;	97%

1-methylbuta-1,3-diene (2004-70-8) + N-(4,4-dimethoxycyclohexa-2,5-dien-1-ylidene)benzamide (106501-69-3) → N-(4-methoxy-8-methyl-5,8-dihydronaphthalen-1-yl)benzamide (174182-76-4)

Conditions	Yield
Stage #1: 1-methylbuta-1,3-diene; N-(4,4-dimethoxycyclohexa-2,5-dien-1-ylidene)benzamide In dichloromethane at 50℃; under 9750780 Torr; for 12h; Diels-Alder reaction; Stage #2: With hydrogenchloride In tetrahydrofuran for 0.5h;	97%

dichloro[η(5):η(1)-N-dimethyl(tetramethylcyclopentadienyl)silyl(tert-butyl)amido]titanium (162763-85-1) + 1-methylbuta-1,3-diene (2004-70-8) → (η5-C5Me4SiMe2N(t)Bu)Ti(1,3-pentadiene)

Conditions	Yield
With nBuLi In hexane refluxing (45 - 60 min); filtering (room temp.), washing (hexane), evapn. (reduced pressure); elem. anal.;	97%

(η6-naphthalene)(η4-1,5-cyclooctadiene)ruthenium(0) (88945-10-2) + 1-methylbuta-1,3-diene (2004-70-8) + tricyclohexylphosphine (2622-14-2) → [ruthenium(0)(η4-(E)-cisoid-1,3-pentadiene)(η4-1,5-COD)(PCy3)] (1373229-54-9)

Conditions	Yield
In acetonitrile; benzene byproducts: naphthalene; under N2, Schlenk and vacuum techniques; suspn. of Ru complex (NCCH3) treated with satd. soln. of CH2CHCHCH2CH3 (benzene) at room temp. for 1 h,then treated with PCy3; evapd. to dryness under vac., extracted with hexane, filtered, concd. (vac.), crystd. at cooling for 2 d (dry ice);	97%

1-methylbuta-1,3-diene (2004-70-8) + N,N’-di-tert-butylthiadiaziridine-1,1-dioxide (40121-14-0, 42028-73-9) → C13H26N2O2S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine In toluene at 65℃; for 3h; Sealed tube; Inert atmosphere; regioselective reaction;	97%

1-methylbuta-1,3-diene (2004-70-8) + 4,4-dimethylcyclohexa-2,5-dienone (1073-14-9) → 4,4,8α-tetramethyl-4aβ,5,8,8aβ-tetrahydro-1(4H)-naphthalenone (70358-61-1, 78006-86-7, 112252-05-8, 112252-06-9)

Conditions	Yield
at 150℃; for 36h;	96%
boron trifluoride diethyl etherate In diethyl ether for 192h; Ambient temperature;	69%
With boron trifluoride diethyl etherate
aluminium trichloride at 40℃; for 21h; Yield given;

1-methylbuta-1,3-diene (2004-70-8) + 2,6-dimethyl-1,4-benzoquinone (527-61-7) → 2,8,8a-trimethyl-4a,5,8,8a-tetrahydronaphthalene-1,4-dione (51315-87-8)

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 0.5h;	96%
With lithium perchlorate In diethyl ether for 0.25h; Ambient temperature;	80%
In benzene
titanium tetrachloride In dichloromethane at -78℃; for 0.5h;

1-methylbuta-1,3-diene (2004-70-8) + benzo[1,4]dithiin-1,1,4,4-tetraoxide (96735-23-8) → 1-Methyl-1,4,4a,10a-tetrahydro-thianthrene 5,5,10,10-tetraoxide (97984-13-9, 98048-74-9)

Conditions	Yield
In 1,2-dichloro-ethane at 50℃; for 10h;	96%

1-methylbuta-1,3-diene (2004-70-8) + methyl 3,6-dioxocyclohexa-1,4-diene-1-carboxylate (3958-79-0) → 5-methyl-1,4-dioxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester

Conditions	Yield
With 2,6-bis[(S)-4-phenyloxazolin-2-yl]pyridine*Sm(OTf)3 In tetrahydrofuran; toluene at -78℃; Diels-Alder cycloaddition;	96%

1-methylbuta-1,3-diene (2004-70-8) + 2-iodo-3-methyl-2-butenoic acid (261927-30-4) → 3-isopropylidene-5-(1-propenyl)dihydrofuran-2-one

Conditions	Yield
With palladium diacetate; 1,1'-bis(di-tertbutylphosphino)ferrocene; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 60℃; for 24h; Cycloaddition;	96%

1-methylbuta-1,3-diene (2004-70-8) → trans-1,4-dibromo-2-pentene (25296-22-4)

Conditions	Yield
With bromine; 1-n-butyl-3-methylimidazolim bromide at 20℃;	95%
With bromine
With bromine In toluene at -15℃;

1-methylbuta-1,3-diene (2004-70-8) + ethene (74-85-1) → (Z)-3-Methyl-1,4-hexadien (16483-83-3)

Conditions	Yield
With CoCl2(1,4-bis(diphenylphosphino)butane); trimethylaluminum In dichloromethane; toluene at -10℃; under 760.051 Torr; for 6h; regioselective reaction;	95%
With (dad)Fe0 under 37503 Torr; Ambient temperature;
With CoCl2(1,4-bis(diphenylphosphino)butane); trimethylaluminum In dichloromethane; toluene at -10℃; under 760.051 Torr;	> 95 %Spectr.

Upstream product

• 110-80-5 2-ethoxy-ethanol 
• 10524-06-8 (±)-(1-chloroethyl)cyclopropane 
• 1574-41-0 Z-piperylene 
• 7371-86-0 2,4-diacetoxy-pentane 
• 142-29-0 cyclopentene 
• 123-91-1 1,4-dioxane 
• 4461-41-0 2-chloro-but-2-ene 
• 689-97-4 3-buten-1-yne 
• 4143-42-4 (Z)-azomethane 
• 504-60-9 penta-1,3-diene 
• 187737-37-7 propene 
• 591-93-5 1,4-Pentadiene 
• 627-20-3 (Z)-pent-2-ene 
• 7642-09-3 cis-3-hexene 

Downstream Products

• 518034-66-7 2,6-dimethyl-cyclohex-3-enecarboxylic acid 
• 6007-71-2 2-methyl-2,5-dihydro-thiophene 1,1-dioxide 
• 1574-41-0 Z-piperylene 
• 101604-13-1 4-(2-methyl-cyclohex-3-enyl)-2-phenyl-but-3-en-2-ol 
• 50983-23-8 methyl 1,4-dihydro-o-toluate 
• 52891-09-5 3-methyl-2-phenyl-3,6-dihydro-2H-[1,2]oxazine 
• 52891-10-8 6-methyl-2-phenyl-3,6-dihydro-2H-[1,2]oxazine 
• 101170-30-3 3-methyl-1t-(2-methyl-cyclohex-3-enyl)-pent-1-en-3-ol 
• 106949-92-2 6-methylcyclohexa-1,4-dienecarboxylic acid 
• 102369-53-9 2,6-dimethyl-cyclohexa-1,4-dienecarboxylic acid 
• 68036-73-7 4-[4-(4-methoxy-phenyl)-1-methyl-but-1-enyl]-morpholine 
• 13358-02-6 3-Methyl-4-cyclohexen-1,1,2,2-tetracarbonitril 
• 60171-29-1 (Pent-3-enyl)-phenylsilan 
• 57449-07-7 (Pent-2-enyl)-phenylsilan 

Relevant articles and documents

Asymmetric Counteranion Directed Catalytic Heck/Tsuji-Trost Annulation of Aryl Iodides and 1,3-Dienes

A chiral anion-mediated asymmetric Heck/Tsuji-Trost reaction of aryl iodides and 1,3-dienes is presented. Chiral indoline derivatives could be afforded with remarkably higher yields and enantioselectivities than our previous chiral ligand-based method. Silver carbonate is employed as both base and halide scavenger to ensure fast and recyclable exchange of the catalytic amount of chiral anions. Fast salt metathesis, as well as the acceleration effect of the chiral anion, could both benefit the stereocontrol of the reaction.

Palladium-Catalyzed Chemoselective Protodecarboxylation of Polyenoic Acids

Conditions for the first palladium-catalyzed chemoselective protodecarboxylation of polyenoic acids to give the desired polyenes in good yields are presented. The reactions proceed under mild conditions using either a Pd(0) or Pd(II) catalyst and tolerate a variety of aryl and aliphatic substitutions. Unique aspects of the reaction include the requirement of phosphines, water, and a polyene adjacent to the carboxylic acid.

Production of renewable 1,3-pentadiene from xylitol via formic acid-mediated deoxydehydration and palladium-catalyzed deoxygenation reactions

A two-step synthetic approach for the production of renewable 1,3-pentadiene was reported: xylitol deoxydehydration (DODH) by formic acid to 2,4-pentadien-1-ol, 1-formate (2E), followed by deoxygenation to 1,3-pentadiene over Pd/C. The overall carbon yield of 1,3-pentadiene reached 51.8% under the optimized conditions.