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Conditions | Yield |
---|---|
With aluminium trichloride; chlorine In dichloromethane | 40% |
Conditions | Yield |
---|---|
With hydrogenchloride; iron(III) chloride at 25℃; im Dunkeln; |
Conditions | Yield |
---|---|
at 400℃; bei der Chlorierung; |
propane
A
1,2-Dichloropropane
B
2,2-dichloropropane
C
1,1-dichloropropane
D
1,3-Dichloropropane
Conditions | Yield |
---|---|
at 400℃; Product distribution; thermische Chlorierung; | |
at 400℃; Product distribution; thermische Chlorierung; |
Conditions | Yield |
---|---|
With clorine In acetonitrile at -25.1℃; Product distribution; Thermodynamic data; ΔE(excit.), var. temperature, other solvents; | |
With chlorine In 1,2-dichloro-benzene at 0℃; Product distribution; oth. temperatures; | |
With chlorine In acetic acid Product distribution; Irradiation; other temperature, other concentration of acetic acid; |
Conditions | Yield |
---|---|
With phosphorus pentachloride | |
With phosphorus pentachloride | |
With molybdenum pentachloride In chloroform; dichloromethane-d2 at 20℃; for 168h; Sealed tube; |
Conditions | Yield |
---|---|
With hydrogenchloride | |
With hydrogenchloride at -35℃; |
prop-1-yne
A
2-chloropropene
B
2,2-dichloropropane
C
trans-1,3-Dichlor-1,3-dimethyl-cyclobutan
D
cis-1,3-Dichlor-1,3-dimethyl-cyclobutan
Conditions | Yield |
---|---|
With hydrogenchloride for 720h; Ambient temperature; Further byproducts given; |
Conditions | Yield |
---|---|
at 209.9℃; Equilibrium constant; |
phosphorus pentachloride
acetone
A
2-chloropropene
B
2,2-dichloropropane
hydrogenchloride
prop-1-yne
A
2-chloropropene
B
2,2-dichloropropane
hydrogenchloride
2-chloropropene
iron(III) chloride
2,2-dichloropropane
Conditions | Yield |
---|---|
at 0℃; im Dunkeln; |
isopropyl chloride
chlorine
A
1,2-Dichloropropane
B
2,2-dichloropropane
Conditions | Yield |
---|---|
im Sonnenlicht; |
tungsten(VI) chloride
acetone
A
2,2-dichloropropane
B
C3H6Cl4O2W
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 168h; Sealed tube; |
2,2-dichloropropane
4-bromo-1,1'-biphenyl
dimethyl(4-biphenyl)silyl chloride
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 3h; Schlenk technique; Glovebox; Stage #2: 2,2-dichloropropane In diethyl ether; hexane at -78 - 20℃; for 15h; Schlenk technique; Glovebox; | 99% |
Conditions | Yield |
---|---|
Stage #1: (E)-2-methyl-4-phenyl-1,3-butadiene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
Stage #1: dibenzoazepine With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 99% |
2,2-dichloropropane
(E)-1,3-decadiene
Conditions | Yield |
---|---|
Stage #1: (E)-1,3-decadiene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 98% |
Stage #1: (E)-1,3-decadiene With 2,6-bis[1-((2-tertbutylphenyl)imino)ethyl]pyridine; cobalt(II) bromide; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Reagent/catalyst; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; |
2,2-dichloropropane
(E)-1-(buta-1,3-dien-1-yl)-4-chlorobenzene
Conditions | Yield |
---|---|
Stage #1: (E)-1-(buta-1,3-dien-1-yl)-4-chlorobenzene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
Stage #1: (Z)-(((4-methylpenta-2,4-dien-1-yl)oxy)methyl)benzene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 1h; | 95% |
Conditions | Yield |
---|---|
Stage #1: (E)-1-(buta-1,3-diene-1-yl)-4-methoxybenzene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 94% |
2,2-dichloropropane
diethyl (E)‐buta‐1,3‐dien‐1‐ylphosphonate
Conditions | Yield |
---|---|
Stage #1: diethyl (E)‐buta‐1,3‐dien‐1‐ylphosphonate With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 93% |
Conditions | Yield |
---|---|
Stage #1: (E)-2-methyl-1-phenyl-1,3-butadiene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 91% |
Conditions | Yield |
---|---|
Stage #1: ethyl (2E)-penta-2,4-dienoate With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 91% |
2,2-dichloropropane
2-allyl-2-(2,4-pentadienyl)malonic acid dimethyl ester
Conditions | Yield |
---|---|
Stage #1: 2-allyl-2-(2,4-pentadienyl)malonic acid dimethyl ester With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 91% |
Conditions | Yield |
---|---|
Stage #1: N-(tert-butoxycarbonyl)-3-pyrroline With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 91% |
2,2-dichloropropane
trimethyltin(IV)chloride
2,2-bis(trimethylstannyl)propane
Conditions | Yield |
---|---|
With Na In ammonia; pentane NH3 (liquid); Na reacted with trimethylchlorostannane in pentane/liq. NH3 under N2, 2,2-dichloropropane added slowly with stirring, NH3 allowed to boil off; extd. with pentane and H2O, pentane layer washed with H2O, evapd. (vac.), treated with H2O2/acetone, stirred, treated with pentane, washed withH2O, pentane layer dried (MgSO4), filtered, concd., distd. (0.01 Torr) at room temp.; elem. anal.; | 90% |
2,2-dichloropropane
Conditions | Yield |
---|---|
In water at 20℃; | 90% |
2,2-dichloropropane
Conditions | Yield |
---|---|
Stage #1: 4,4,5,5- tetramethyl-2-[(1E)-3-methylbuta-1,3-dien-1-yl]-1,3,2-dioxaborolane With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 90% |
2,2-dichloropropane
1,2-cyclooctene
9,9-dimethylbicyclo[6.1.0]nonane
Conditions | Yield |
---|---|
Stage #1: 1,2-cyclooctene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 83% |
2,2-dichloropropane
1-indene
1,1-Dimethyl-1,1a,6,6a-tetrahydro-cyclopropa[a]indene
Conditions | Yield |
---|---|
Stage #1: 1-indene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 82% |
2,2-dichloropropane
1-chloro-1-methylethylphosphonic dichloride
Conditions | Yield |
---|---|
With aluminium trichloride; phosphorus trichloride for 3h; | 81% |
Conditions | Yield |
---|---|
Stage #1: cyclopentene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 80% |
Conditions | Yield |
---|---|
Stage #1: (E)-benzyl(penta-2,4-dien-1-yl)sulfane With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 79% |
2,2-dichloropropane
4-(4-bromophenyl)bromobenzene
[CpZrCl2{CpSiMe2C6H4}]2
Conditions | Yield |
---|---|
Stage #1: 4-(4-bromophenyl)bromobenzene With n-butyllithium In diethyl ether; hexane at 0 - 20℃; for 5h; Schlenk technique; Glovebox; Stage #2: 2,2-dichloropropane In diethyl ether; hexane at -78 - 20℃; for 15h; Schlenk technique; Glovebox; | 74% |
Conditions | Yield |
---|---|
Stage #1: (E)‐2‐(buta-1,3‐dien‐1‐yl)furan With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 74% |
2,2-dichloropropane
(E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene
Conditions | Yield |
---|---|
Stage #1: (E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 72% |
2,2-dichloropropane
pinacol vinylboronate
2‐(2,2‐dimethylcyclopropyl)‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane
Conditions | Yield |
---|---|
Stage #1: pinacol vinylboronate With C27H31Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Inert atmosphere; Glovebox; | 69% |
Conditions | Yield |
---|---|
Stage #1: norbornene With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 67% |
2,2-dichloropropane
2,3-dihydro-1,3-di(neopentyl)-1H-1,3,2-benzodiazasilol-2-ylidene
2'-chloro-2-(1-chloro-1-methyl-ethyl)-1,3,1',3'-tetrakis-(2,2-dimethyl-propyl)-2,3,2',3'-tetrahydro-1H,1'H-[2,2']bi[benzo[1,3,2]diazasilolyl]
Conditions | Yield |
---|---|
In hexane at 20℃; for 16h; | 64% |
Conditions | Yield |
---|---|
Stage #1: (E)‐N,4‐dimethyl‐N‐(penta‐2,4‐dien‐1‐yl)benzenesulfonamide With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 57% |
Conditions | Yield |
---|---|
Stage #1: (2E)-4-methylpenta-2,4-dien-1-ol With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 57% |
Conditions | Yield |
---|---|
Stage #1: (E)-1-phenyl-penta-2,4-dien-1-one With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction; | 54% |
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