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cis-2,2-difluoro-1-(1-propenyl)cyclopropane
A
Z-piperylene
B
cis-5,5-difluoro-1,3-hexadiene
C
4,4-difluoro-3-methylcyclopentene
D
3,3-difluoro-5-methylcyclopentene
Conditions | Yield |
---|---|
at 293.5℃; for 3.66667h; | A 15% B 24% C 12% D 49% |
In cyclohexane; pentane at 262.2 - 321.6℃; Thermodynamic data; Kinetics; Ea, ΔH*, ΔS*; |
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% |
isobutene
A
1-butylene
B
(Z)-2-Butene
C
2-methyl-but-2-ene
D
Z-piperylene
E
1-methylbuta-1,3-diene
F
propene
G
methane
H
trans-2-Butene
I
(Z)-pent-2-ene
J
(E)-pent-2-ene
K
ethane
L
propane
M
Isobutane
N
methylbutane
O
ethene
P
1-penten
Q
Cyclopentane
R
2-Methyl-1-butene
S
3-Methyl-1-butene
T
cyclopentene
U
n-butane
V
pentane
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% |
Conditions | Yield |
---|---|
silver trifluoromethanesulfonate In acetonitrile for 2h; Irradiation; | 22% |
With hydrocarbon; ammonium chloride; copper(l) chloride in sehr verduennter HCl in Gegenwart von etwas Kupferwolle bei 25grad,fraktionierte Zersetzung der CuCl-Komplexverbindungen durch sehr langsames Erwaermen bis auf 100grad und fraktionierte Destillation des anteils vom Kp:43.6-44.0grad; | |
Ambient temperature; Irradiation; Yield given; | |
under 0.1 Torr; Product distribution; Irradiation; |
Conditions | Yield |
---|---|
With maleic anhydride; hydrogen at 100℃; dabei werden die trans-Form und Cyclopentadien infolge Umsetzung mit Maleinsaeureanhydrid zurueckgehalten.; |
2,4-diacetoxy-pentane
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
1,4-Pentadiene
Conditions | Yield |
---|---|
at 575 - 600℃; |
(Z)-pent-2-ene
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
methane
D
(E)-pent-2-ene
E
ethene
F
acetaldehyde
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. |
1-penten
A
2-pentyloxirane
B
Z-piperylene
C
1-methylbuta-1,3-diene
D
propene
E
ethene
F
buta-1,3-diene
Conditions | Yield |
---|---|
With (per)acetylperoxyboric acid; hydrogen; oxygen at 480℃; Mechanism; | A 18.7 % Chromat. B 4.3 % Chromat. C 11.0 % Chromat. D 18.9 % Chromat. E 18.0 % Chromat. F 12.2 % Chromat. |
ethenylcyclopropane
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
1,4-Pentadiene
D
cyclopenta-1,3-diene
Conditions | Yield |
---|---|
In gas under 0.2 - 10 Torr; Irradiation; 933 cm1- CO2 laser pulses; Further byproducts given. Title compound not separated from byproducts; | A 4 % Chromat. B 4 % Chromat. C 9 % Chromat. D 48 % Chromat. |
ethenylcyclopropane
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
1,4-Pentadiene
D
cyclopenta-1,3-diene
E
cyclopentene
Conditions | Yield |
---|---|
In gas under 0.2 - 10 Torr; Product distribution; Irradiation; laser frequency, laser intensity; | A 4 % Chromat. B 4 % Chromat. C 9 % Chromat. D 48 % Chromat. E 36 % Chromat. |
ethenylcyclopropane
A
Z-piperylene
B
1,4-Pentadiene
C
cyclopenta-1,3-diene
D
cyclopentene
Conditions | Yield |
---|---|
In gas under 0.2 - 10 Torr; Irradiation; 933 cm1- CO2 laser pulses; Further byproducts given. Title compound not separated from byproducts; | A 4 % Chromat. B 9 % Chromat. C 48 % Chromat. D 36 % Chromat. |
trimethyl-pent-4-enyl-ammonium; hydroxide
A
Z-piperylene
B
1-methylbuta-1,3-diene
Conditions | Yield |
---|---|
at 150 - 160℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
endo-6-Methylbicyclo<3.1.0>hexan-3-one
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
3-methyl-1,4-pentadiene
trans-1-Methyl-2-vinylcyclopropane
cis-1-Methyl-2-vinylcyclopropane
Conditions | Yield |
---|---|
at 150℃; under 50 Torr; for 6h; Quantum yield; Mechanism; Irradiation; various temp. and pressure; |
exo-6-Methylbicyclo<3.1.0>hexan-3-one
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
3-methyl-1,4-pentadiene
trans-1-Methyl-2-vinylcyclopropane
cis-1-Methyl-2-vinylcyclopropane
Conditions | Yield |
---|---|
at 150℃; under 50 Torr; for 6h; Quantum yield; Mechanism; Irradiation; various temp. and pressure; |
cyclobut-2-enylmethyl bromide
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
1,4-Pentadiene
D
3-methylcyclobutene
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride In various solvent(s) at 50℃; for 1h; Irradiation; | |
With tri-n-butyl-tin hydride In various solvent(s) at 77℃; for 1h; Mechanism; Rate constant; Thermodynamic data; Irradiation; further temperatures; ΔE(excit), non-perfect synchronisation of β-scission with product stabilisation in radical ring-opening; |
(E)-5-Trimethylsilanyl-pent-3-en-2-ol
A
Z-piperylene
B
1-methylbuta-1,3-diene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride |
1-bromo-3-methyl-2-chloromethylcyclopropane
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
2-methylbicyclo<1.1.0>butane
D
isoprene
Conditions | Yield |
---|---|
With iodine; magnesium; ethylene dibromide In tetrahydrofuran for 2h; Heating; Yield given. Yields of byproduct given; |
cyclopentene
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
1,4-Pentadiene
D
cyclopenta-1,3-diene
Conditions | Yield |
---|---|
Product distribution; multiple-photon decomposition, effect of pressure fluences and irradiation times; |
1,3-dimethylcyclopropene
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
2-Pentyne
D
penta-2,3-diene
E
penta-1,2-diene
F
1-Ethylcyclopropene
Conditions | Yield |
---|---|
at 482℃; under 50 Torr; other temp.; Ea, lg A; |
1-Ethylcyclopropene
A
Z-piperylene
B
1-methylbuta-1,3-diene
C
2-Pentyne
D
penta-2,3-diene
E
penta-1,2-diene
F
1,3-dimethylcyclopropene
Conditions | Yield |
---|---|
at 472℃; under 50 Torr; other temp.; Ea, lg A; |
pent-1->3-enyl
Z-piperylene
Conditions | Yield |
---|---|
at 24.9℃; Thermodynamic data; ΔH; |
Conditions | Yield |
---|---|
In benzene educts in stochiometric amt., small reacn. rate; | 100% |
Z-piperylene
2-iodo-3-methyl-2-butenoic acid
Conditions | Yield |
---|---|
With palladium diacetate; 1,1'-bis(di-tertbutylphosphino)ferrocene; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 60℃; for 24h; Cycloaddition; | 99% |
Z-piperylene
Conditions | Yield |
---|---|
With tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) In 1,2-dichloro-ethane at 60℃; for 6h; Inert atmosphere; enantioselective reaction; | 99% |
Z-piperylene
N-phenylbenzohydrazonoyl chloride
1,3-Diphenyl-5-(cis-1-propenyl)-2-pyrazolin
Conditions | Yield |
---|---|
With triethylamine In benzene at 40℃; | 96% |
With Allyl acetate; triethylamine In benzene at 40℃; Kinetics; competition const., rel. velocity const.; |
Z-piperylene
diethyl (2-iodobenzyl)malonate
((E)-3-Propenyl)-3,4-dihydro-1H-naphthalene-2,2-dicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; palladium diacetate; sodium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 60℃; for 48h; Product distribution; Mechanism; var. 1,3-dienes, var. aryl halides, var. reagents and reaction conditions; | 95% |
With tetrabutyl-ammonium chloride; palladium diacetate; sodium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 60℃; for 48h; | 95% |
Z-piperylene
trans-1,4-dibromo-2-pentene
Conditions | Yield |
---|---|
With bromine; 1-n-butyl-3-methylimidazolim bromide at 20℃; | 95% |
Z-piperylene
Conditions | Yield |
---|---|
Stage #1: Z-piperylene; 1-(methylsulfonyl)-4-(1,4-dioxaspiro[4.5]dec-6-en-6-yl)-1H-1,2,3-triazole With tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) In 1,2-dichloro-ethane at 60℃; for 6h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In tetrahydrofuran at 0 - 22℃; for 6h; Inert atmosphere; enantioselective reaction; | 94% |
Z-piperylene
Conditions | Yield |
---|---|
With tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) In 1,2-dichloro-ethane at 60℃; for 6h; Inert atmosphere; enantioselective reaction; | 94% |
Z-piperylene
(E)-3-(methoxycarbonyl)methylene-1,3-dihydroindol-2-one
C16H17NO3
Conditions | Yield |
---|---|
In toluene at 120℃; for 5h; | 90% |
Z-piperylene
Conditions | Yield |
---|---|
With tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) In 1,2-dichloro-ethane at 60℃; for 6h; Inert atmosphere; enantioselective reaction; | 90% |
(η6-naphthalene)(η4-1,5-cyclooctadiene)ruthenium(0)
Z-piperylene
triphenylphosphine
Conditions | Yield |
---|---|
In acetonitrile byproducts: naphthalene; under N2, Schlenk and vacuum techniques; suspn. of Ru complex (NCCH3) treated with CH2CHCHCH2CH3 at room temp. for 1 h, then treated with PPh3; | 88% |
Z-piperylene
Conditions | Yield |
---|---|
With tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) In 1,2-dichloro-ethane at 60℃; for 6h; Inert atmosphere; enantioselective reaction; | 88% |
Conditions | Yield |
---|---|
In benzene diene added to suspn. of Nb-complex (Ar, 5°C), heating (60°C, 4 h); evapn., extn. (hexane), crystn. (-20°C); | 87% |
Z-piperylene
pentamethylcyclopentadienylruthenium dichloride
(η5-pentamethylcyclopentadienyl)(η5-pentadienyl)ruthenium
Conditions | Yield |
---|---|
With Zn In ethanol byproducts: HCl; dissolving (C5Me5RuCl2)n and (Z)-1,3-pentadiene in EtOH under N2, stirring (2 h), addn. of Zn powder, further stirring (1 h); filtration (fritted disk covered with cotton wool), removing solvent (vac.), dissolving in hexane, filtration (Al2O3, grade IV), evapg. solvent, drying (high vac.); elem. anal.; | 85% |
Z-piperylene
9-(selenocyanato)fluorene
3',6'-dihydro-3'-methylspiro<9H-fluorene-9,2'-<2'H>selenopyran>
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; dichloromethane at 25℃; | 82% |
Z-piperylene
4-cyclohex-1-en-1-yl-1-(methylsulfonyl)-1H-1,2,3-triazole
Conditions | Yield |
---|---|
With tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) In 1,2-dichloro-ethane at 60℃; for 6h; Inert atmosphere; enantioselective reaction; | 81% |
Z-piperylene
(E)-methyl 2-diazo-4-phenylbut-3-enoate
Conditions | Yield |
---|---|
In pentane | 79% |
Z-piperylene
(Z)-2-bromo-3-phenylacrylic acid
Conditions | Yield |
---|---|
With palladium diacetate; 1,1'-bis(di-tertbutylphosphino)ferrocene; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 60℃; for 24h; Cycloaddition; | 78% |
Z-piperylene
ethenetetracarbonitrile
3-Methyl-4-cyclohexen-1,1,2,2-tetracarbonitril
Conditions | Yield |
---|---|
In dichloromethane at 20℃; Rate constant; Kinetics; | 75% |
In dichloromethane for 1008h; Ambient temperature; | 75% |
Z-piperylene
4-chloro-benzenesulfenyl chloride
threo-1-chloro-4-<(2-chloro-1-methyl-3-butenyl)thio>benzene
B
(Z)-1-chloro-4-<(2-chloro-3-pentenyl)thio>benzene
Conditions | Yield |
---|---|
In various solvent(s) at 25℃; Rate constant; | A 27% B 73% |
Z-piperylene
6-(tert-butylperoxy)bicyclo[4.4.0]deca-1,4-dien-3-one
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 0℃; | 73% |
Z-piperylene
4-benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione
Conditions | Yield |
---|---|
In toluene at 100℃; for 24h; | 73% |
Z-piperylene
C6H9N3O2S
Conditions | Yield |
---|---|
With tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) In 1,2-dichloro-ethane at 60℃; for 6h; Inert atmosphere; enantioselective reaction; | 71% |
Conditions | Yield |
---|---|
In pentane Degassing of mixt., sealing in react. tube, keeping at -30°C for 6 h, removal of solvent and excess diene, addn. of isooctane, heating (30 min, 120°C).; Vac. distn., MS, (1)H-, (19)F- and (13)C-NMR, elem. anal.; | 70% |
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; sodium acetate; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24h; | 68% |
Z-piperylene
ethyl (E)-2-diazo-6-phenyl-1-hexa-3,5-dienoate
ethyl trans-4-methyl-3-((E)-2-phenylethenyl)cyclohepta-1,5-diene-1-carboxylate
Conditions | Yield |
---|---|
rhodium(II) hexanoate In dichloromethane a) 10 deg C, 30 min, b) 10 min, reflux; | 68% |
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: MgCl2; excess of diene, stirring (-30°C); evapn. (vac., -30°C), extraction (pentane, -30°C), concn.,crystn. (-78°C); elem. anal.; | 63% |
Z-piperylene
Conditions | Yield |
---|---|
With rhodium(II) (N-dodecylbenzenesulfonyl)prolinate In hexane at -78 - 20℃; | 62% |
Conditions | Yield |
---|---|
With triphenyl phosphite; copper(l) chloride In benzene-d6 at 65℃; for 6h; | 58% |
Conditions | Yield |
---|---|
In not given byproducts: C6H10; under Ar, reacting the Cr complex with a mixt. of cis- and trans-piperylene (7:13); | 58% |
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