15022-08-9

Basic information

• Product Name: DIALLYL CARBONATE
• Synonyms: Allyl carbonate;Carbonic acid, di-2-propenyl ester;Carbonic acid, diallyl ester;carbonicacid,di-2-propenylester;DIALLYL CARBONATE;Carbonic acid diallyl;Carbonic acid O,O-diallyl ester;Diallyl carbonate 99%
• CAS NO: 15022-08-9
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.15
• EINECS: 239-106-9
• Product Categories: monomer;Allyl Monomers;Monomers;Polymer Science
• Mol File: 15022-08-9.mol
• Article Data: 27

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 95-97 °C60 mm Hg(lit.)
• Flash Point: 138 °F
• Appearance: /
• Density: 0.991 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.34mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: DIALLYL CARBONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIALLYL CARBONATE(15022-08-9)
• EPA Substance Registry System: DIALLYL CARBONATE(15022-08-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 15022-08-9(Hazardous Substances Data)

Usage

Uses

Transesterification of diallyl carbonate with glycerol in the presence of a catalyst (Pd/PPh3), generates glycerol carbonate.

General Description

Diallyl carbonate is an acrylating agent. Allyl carbonates are widely employed in Tsuji-Trost allylation, generating carbanion, boronate, phosphide, amide and alkoxide, nucleophiles in situ and improving reaction rates over allyl acetate. Allyl carbonates are also of considerable interest for the intramolecular decarboxylative assymetric couplings.

InChI:InChI=1/C7H10O3/c1-3-5-9-7(8)10-6-4-2/h3-4H,1-2,5-6H2

Synthetic route

allyl alcohol (107-18-6) + carbonic acid dimethyl ester (616-38-6) → diallylcarbonate (15022-08-9)

Conditions	Yield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In neat (no solvent) at 80℃; under 760.051 Torr; for 16h; Inert atmosphere; Green chemistry;	95%
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 80 - 120℃; for 48h;	61%
With potassium carbonate at 70℃; for 6h;	53%
With sodium methylate at 60℃; for 1h; Inert atmosphere;	2 %Chromat.

carbon dioxide (124-38-9) + allyl alcohol (107-18-6) → Allyl ether (557-40-4) + diallylcarbonate (15022-08-9)

Conditions	Yield
With copper (I) iodide; dicyclohexyl-carbodiimide at 64.85℃; under 37503 Torr; for 4h;	A 6% B 93%
With dicyclohexyl-carbodiimide In toluene at 64.85℃; under 37503 Torr; for 6h;	A n/a B 3.3%

carbon dioxide (124-38-9) + allyl alcohol (107-18-6) + O-allyl-N,N'-dicyclohexyl isourea (92954-34-2) → Allyl ether (557-40-4) + diallylcarbonate (15022-08-9)

Conditions	Yield
at 64.85℃; under 37503 Torr; for 2h;	A 7% B 91%

allyl alcohol (107-18-6) + trichloromethyl chloroformate (503-38-8) → diallylcarbonate (15022-08-9)

Conditions	Yield
With pyridine In diethyl ether a) 0 deg C, 1 h, b) 25 deg C, 5 h;	85%
With pyridine In diethyl ether at 25℃; for 5h;	67%

carbon dioxide (124-38-9) + allyl alcohol (107-18-6) → diallylcarbonate (15022-08-9)

Conditions	Yield
With 2-Cyanopyridine; cerium(IV) oxide at 119.84℃; under 37503.8 Torr; for 48h; Autoclave;	76%
With dichloromethane; caesium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; under 760.051 Torr; for 24h;	58%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 18h;	40%
With carbon tetrabromide; tributylphosphine; 2-cyclohexyl-1,1,3,3-tetramethylguanidine In N,N-dimethyl-formamide at 20℃; for 2h; Condensation;	64.1 % Spectr.

allyl alcohol (107-18-6) → diallylcarbonate (15022-08-9)

Conditions	Yield
With lanthanum(III) chloride; urea at 180℃; for 6h; Reagent/catalyst; Autoclave;	60.7%

potassium hydrogencarbonate (298-14-6) + allyl bromide (106-95-6) → Allyl ether (557-40-4) + diallylcarbonate (15022-08-9)

Conditions	Yield
tetrabutyl phosphonium bromide In various solvent(s) at 150℃; Solvent: NMP;	A n/a B 50%

allyl alcohol (107-18-6) + carbonic acid dimethyl ester (616-38-6) → allyl methyl carbonate (35466-83-2) + diallylcarbonate (15022-08-9)

Conditions	Yield
Stage #1: allyl alcohol; carbonic acid dimethyl ester at 80℃; Stage #2: With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 80℃; for 1h;	A 50% B n/a
sodium methylate at 23℃; Inert atmosphere of nitrogen;
sodium methylate at 23℃; Inert atmosphere of nitrogen;
With sodium aluminate at 20 - 90℃; for 24h;

(2-oxo-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (949895-84-5) + allyl alcohol (107-18-6) → diallylcarbonate (15022-08-9) + allyl glycidyl carbonate (68404-09-1)

Conditions	Yield
Stage #1: allyl alcohol With sodium hydride In tetrahydrofuran Stage #2: (2-oxo-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate With tetrabutylammomium bromide In tetrahydrofuran at -70 - 20℃;	A 12% B 47%

tri-n-propylamine (102-69-2) + carbon dioxide (124-38-9) → diallylcarbonate (15022-08-9) + propyl N,N-di-propylcarbamate (27031-52-3) + allyl n-propyl carbonate

Conditions	Yield
With allyl alcohol; acetylene at 160℃; for 16h;	A 6% B 4% C 21%

tri-n-propylamine (102-69-2) + carbon dioxide (124-38-9) + allyl alcohol (107-18-6) → diallylcarbonate (15022-08-9) + propyl N,N-di-propylcarbamate (27031-52-3) + allyl n-propyl carbonate

Conditions	Yield
With acetylene at 160℃; for 16h;	A 6% B 4% C 21%

carbon dioxide (124-38-9) + triethylamine (121-44-8) + allyl alcohol (107-18-6) → diallylcarbonate (15022-08-9) + ethyl N,N-diethylcarbamate (3553-80-8) + allyl ethyl carbonate (1469-70-1)

Conditions	Yield
With acetylene at 160℃; for 16h;	A 8% B 14% C 19%

carbon dioxide (124-38-9) + allyl alcohol (107-18-6) → diallylcarbonate (15022-08-9) + ethyl N,N-diethylcarbamate (3553-80-8) + allyl ethyl carbonate (1469-70-1)

Conditions	Yield
With triethylamine; acetylene at 160℃; for 16h;	A 8% B 14% C 19%

phosgene (75-44-5) + allyl alcohol (107-18-6) → diallylcarbonate (15022-08-9) + Allyl chloroformate (2937-50-0)

allyl alcohol (107-18-6) + Diethyl carbonate (105-58-8) → diallylcarbonate (15022-08-9)

Conditions	Yield
With ethanol; sodium ethanolate
With sodium

diallyl oxalate (615-99-6) + sodium → diallylcarbonate (15022-08-9) + carbon monoxide

carbon dioxide (124-38-9) + allyl alcohol (107-18-6) + N,N'-dicyclohexyl-O-methyl isourea (6257-10-9) → allyl methyl carbonate (35466-83-2) + diallylcarbonate (15022-08-9)

Conditions	Yield
In acetonitrile at 59.85℃;

2-methoxyethoxyethoxyethyl allyl carbonate + diethylene glycol diallyl dicarbonate → diallylcarbonate (15022-08-9)

carbon dioxide (124-38-9) + N,N-Dimethylformamide diallyl acetal (61296-25-1) → diallylcarbonate (15022-08-9)

Conditions	Yield
In dimethylsulfoxide-d6 at 100℃; under 15201 Torr; for 24h; Pressure; Inert atmosphere;	73 %Spectr.

carbon dioxide (124-38-9) + N,N-Dimethylformamide diallyl acetal (61296-25-1) + N,N-dimethylformamide dibenzyl acetal (2016-04-8) → diallylcarbonate (15022-08-9) + DBC (3459-92-5) + O-Alloc benzyl alcohol (22768-01-0)

Conditions	Yield
In dimethyl sulfoxide at 100℃; under 760.051 Torr; for 24h; Inert atmosphere; Overall yield = 44 %;

[1,3]-dioxolan-2-one (96-49-1) + allyl alcohol (107-18-6) → diallylcarbonate (15022-08-9)

Conditions	Yield
With sodium methylate at 60℃; for 1h; Inert atmosphere;	2 %Chromat.

1,3-benzodioxol-2-one (2171-74-6) + allyl alcohol (107-18-6) → diallylcarbonate (15022-08-9)

Conditions	Yield
With sodium methylate In neat (no solvent) at 60℃; for 1h; Catalytic behavior; Temperature; Reagent/catalyst; Inert atmosphere;	73 %Chromat.

1,3-benzodioxol-2-one (2171-74-6) + allyl alcohol (107-18-6) → diallylcarbonate (15022-08-9) + benzene-1,2-diol (120-80-9)

Conditions	Yield
With sodium methylate at 60℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere;	A 73 %Chromat. B n/a

diallylcarbonate (15022-08-9) + 1'-<(trimethylsilyl)oxy>-2'-methylspiro<1,3-dioxolane-2,4'-cyclohexene> (91759-99-8) → 7-allyl-7-methyl-1,4-dioxaspiro[4.5]decan-8-one (473714-50-0)

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate; tris-(dibenzylideneacetone)dipalladium(0); (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol In tetrahydrofuran at 25℃; for 2h; Product distribution / selectivity;	99%

diallylcarbonate (15022-08-9) + Benzoylformic acid (611-73-4) → (E)-1-phenyl-2-buten-1-one (35660-91-4, 35845-66-0, 495-41-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); Tri(p-tolyl)phosphine In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	99%

diallylcarbonate (15022-08-9) + tert-butyl 3-hydroxy-3-(1-methyl-4-nitro-1H-pyrazol-5-yl)propanoate (1586042-83-2) → tert-butyl 3-(allyloxy)-3-(1-methyl-4-nitro-1H-pyrazol-5-yl)propanoate (1586042-85-4)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In 1,4-dioxane at 65℃; for 1h; Inert atmosphere;	99%

diallylcarbonate (15022-08-9) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → allyl 1-hydroxy-3,4-dihydronaphthalene-2-carboxylate

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 12h;	99%

diallylcarbonate (15022-08-9) + 2-amino-phenol (95-55-6) → N-allyl benzoxazol-2-one (13444-14-9)

Conditions	Yield
With potassium carbonate at 130℃; for 16h;	98%

diallylcarbonate (15022-08-9) + (E)-1-(3-hydroxyphenyl)-2-(3-hydroxyphenyl)ethene (70709-65-8, 135781-00-9, 143207-60-7) → (E)-1,2-bis(3-(allyloxy)phenyl)ethene

Conditions	Yield
With tetrabutylammomium bromide at 120℃; for 20h; Inert atmosphere;	98%

diallylcarbonate (15022-08-9) + 2-([1,1’-biphenyl]-4-yl)-2-oxoacetic acid (5449-21-8) → (E)-1-([1,1'-biphenyl]-4-yl)but-2-en-1-one (71823-67-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); Tri(p-tolyl)phosphine In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	97%

diallylcarbonate (15022-08-9) + (2-ethylcyclohex-1-enyloxy)trimethylsilane (89683-95-4) → (+)-2-allyl-2-ethylcyclohexanone (812639-08-0)

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate; tris-(dibenzylideneacetone)dipalladium(0); (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol In tetrahydrofuran at 25℃; for 3h; Product distribution / selectivity;	96%
With tris-(dibenzylideneacetone)dipalladium(0); tetrabutylammonium triphenyldifluorosilicate; (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol In tetrahydrofuran at 25℃; for 4h; asymmetric Tsuji allylation; Inert atmosphere; optical yield given as %ee;	96%

diallylcarbonate (15022-08-9) + 4,4-ethylenedioxy-piperidine (177-11-7) → allyl 1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate

Conditions	Yield
With 2-hydroxypyridin; zirconium(IV) tert-butoxide at 80℃; for 12h;	95%

diallylcarbonate (15022-08-9) + benzylamine (100-46-9) → benzyl carbamic acid allyl ester (104669-74-1)

Conditions	Yield
With 2-hydroxypyridin; zirconium(IV) tert-butoxide at 80℃; for 12h;	95%

diallylcarbonate (15022-08-9) + 1-trimethylsilyloxy-2-methyl-1-cyclohexene (19980-35-9) → (2S)-2-methyl-2-(2-propen-1-yl)cyclohexanone (812639-07-9)

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate; tris-(dibenzylideneacetone)dipalladium(0); (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol In tetrahydrofuran at 25℃; for 2h; Product distribution / selectivity;	95%

diallylcarbonate (15022-08-9) + aniline (62-53-3) → N-allyl-N-phenylamine (589-09-3)

Conditions	Yield
With NaY at 130℃; for 1.66667h;	94%

diallylcarbonate (15022-08-9) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → allyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate (912294-64-5)

Conditions	Yield
Stage #1: 3,4-dihydronaphthalene-1(2H)-one With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #2: diallylcarbonate In tetrahydrofuran; mineral oil for 16h; Inert atmosphere;	94%
With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 16h; Inert atmosphere;	93%
Stage #1: 3,4-dihydronaphthalene-1(2H)-one With sodium hydride In tetrahydrofuran Stage #2: diallylcarbonate In tetrahydrofuran
Stage #1: 3,4-dihydronaphthalene-1(2H)-one With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: diallylcarbonate In tetrahydrofuran at 20℃; for 16h;
Stage #1: 3,4-dihydronaphthalene-1(2H)-one With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.25h; Stage #2: diallylcarbonate In tetrahydrofuran; mineral oil at 20℃; for 16h;

diallylcarbonate (15022-08-9) + 1-<(trimethylsilyl)oxy>-2-methylcycloheptene (64639-26-5) → (S)-2-allyl-2-methylcycloheptan-1-one

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate; tris-(dibenzylideneacetone)dipalladium(0); (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol In tetrahydrofuran at 25℃; for 2h; Product distribution / selectivity;	94%

diallylcarbonate (15022-08-9) + 1-naphthylglyoxylic acid (26153-26-4) → (E)-1-(naphthalen-1-yl)but-2-en-1-one (128113-46-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); Tri(p-tolyl)phosphine In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	94%

diallylcarbonate (15022-08-9) + allyl acetoacetate (1118-84-9) → α,α,α-triallyacetone (76003-04-8)

Conditions	Yield
palladium; triphenylphosphine In tetrahydrofuran	93%

diallylcarbonate (15022-08-9) + 4-oxo-4,5,6,7-tetrahydrobenzofuran (16806-93-2) → allyl 4-oxo-4,5,6,7-tetrahydrobenzofuran-5-carboxylate

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 16h; Inert atmosphere;	93%

diallylcarbonate (15022-08-9) + O-ethyl S-(2-oxotetrahydrothiophen-3-yl)carbonodithioate → bis(2-((ethoxycarbonothioyl)thio)-3-(2-oxotetrahydrothiophen-3-yl)propyl) carbonate

Conditions	Yield
Stage #1: diallylcarbonate; O-ethyl S-(2-oxotetrahydrothiophen-3-yl)carbonodithioate In ethyl acetate at 80℃; for 0.25h; Inert atmosphere; Stage #2: With dilauryl peroxide In ethyl acetate for 5h; Inert atmosphere;	93%

diallylcarbonate (15022-08-9) + 1-methyl-4-(benzylsulfonyl)benzene (5395-20-0) → 1-Methyl-4-(1-phenyl-but-3-ene-1-sulfonyl)-benzene (71376-51-7)

Conditions	Yield
With 1,2-bis-(diphenylphosphino)ethane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 65℃; for 3h;	92%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 65℃; for 1h;	92%

(±)-5-methoxy-2-methylindoline (41568-27-8) + diallylcarbonate (15022-08-9) → (S)-3-methylindoline allyl carbamate + (3R)-2,3-dihydro-3-methyl-1H-indole

Conditions	Yield
With Candida antarctica lipase B In various solvent(s) at 30℃; for 10h;	A 92% B 88%

diallylcarbonate (15022-08-9) + Trimethylenediamine (109-76-2) → (3-aminopropyl)carbamic acid allyl ester

Conditions	Yield
With water at 20℃; for 3h;	92%

p-aminomethylbenzoic acid (56-91-7) + diallylcarbonate (15022-08-9) → Alloc-Amb-OH (173153-42-9)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 20℃;	92%

diallylcarbonate (15022-08-9) + phenylacetonitrile (140-29-4) → 2-phenylpent-4-enenitrile (5558-87-2)

Conditions	Yield
With 1,2-bis-(diphenylphosphino)ethane; Pd(dibenzylideneacetone)2 chloroform adduct In tetrahydrofuran at 65℃; for 2h;	91%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 65℃; for 1h;	91%

diallylcarbonate (15022-08-9) + benzeneacetic acid methyl ester (101-41-7) → methyl allylphenylacetate (14815-73-7)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 65℃; for 1h;	91%

benzyl (2SR,3aSR,7aSR)-octahydroindole-2-carboxylate + diallylcarbonate (15022-08-9) → benzyl (2R,3aR,7aR)-octahydroindole-2-carboxylate (760916-37-8) + benzyl (2S,3aS,7aS)-N-(allyloxycarbonyl)-octahydroindole-2-carboxylate

Conditions	Yield
With IMB-104 Candida antarctica lipase A In various solvent(s) at 30℃; for 72h;	A 90% B 91%

diallylcarbonate (15022-08-9) + inden-1-one (83-33-0) → allyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate

Conditions	Yield
Stage #1: inden-1-one With sodium hydride In tetrahydrofuran at 0 - 23℃; Inert atmosphere; Stage #2: diallylcarbonate In tetrahydrofuran at 23℃; for 16h; Inert atmosphere;	91%
Stage #1: inden-1-one With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.25h; Stage #2: diallylcarbonate In tetrahydrofuran; mineral oil for 16h;	62%
Stage #1: inden-1-one With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: diallylcarbonate In tetrahydrofuran at 20℃; for 16h;
Stage #1: inden-1-one With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.25h; Stage #2: diallylcarbonate In tetrahydrofuran; mineral oil at 20℃; for 16h;

diallylcarbonate (15022-08-9) + 5-fluoro-3,4-dihydronaphthalen-1(2H)-one (93742-85-9) → allyl 5-fluoro-1-hydroxy-3,4-dihydronaphthalene-2-carboxylate

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 21h;	91%

Upstream product

• 75-44-5 phosgene 
• 107-18-6 allyl alcohol 
• 105-58-8 Diethyl carbonate 
• 503-38-8 trichloromethyl chloroformate 
• 298-14-6 potassium hydrogencarbonate 
• 106-95-6 allyl bromide 
• 102-69-2 tri-n-propylamine 
• 124-38-9 carbon dioxide 
• 121-44-8 triethylamine 
• 615-99-6 diallyl oxalate 
• 92954-34-2 O-allyl-N,N'-dicyclohexyl isourea 
• 6257-10-9 N,N'-dicyclohexyl-O-methyl isourea 
• 949895-84-5 (2-oxo-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 223741-66-0 1-N-(allyloxycarbonyl)-1,2-diaminoethane 
• 36321-95-6 6-methyl-2-allylcyclohexanone 
• 85217-80-7 hexa-1,5-dien-3-yl p-tolyl sulphone 
• 84603-00-9 4-(p-tolylsulphonyl)-4-vinyl-1,6-heptadiene 
• 84603-00-9 1-Methyl-4-[((E)-nona-1,5,8-triene)-3-sulfonyl]-benzene 
• 29517-58-6 1-allylcyclohexanecarbaldehyde 
• 95514-61-7 1-((E)-6,10-Dimethyl-undeca-1,5,9-triene-4-sulfonyl)-4-methyl-benzene 
• 56620-95-2 3-methyl-2-allylcyclohexanone 
• 1745-31-9 allyl vinylacetate 
• 95514-58-2 2-Phenyl-2-(tetrahydro-pyran-2-yloxy)-pent-4-enenitrile 
• 128586-68-5 2-allyl-3-phenylpropionaldehyde 
• 53546-37-5 α-allylbutyrophenone 
• 94-66-6 2-allylcyclohexan-1-one 
• 5277-36-1 2,2-diallylcyclohexanone 

Relevant articles and documents

Highly efficient Tsuji-Trost allylation in water catalyzed by Pd-nanoparticles

Palladium nanoparticles stabilized by poly(vinylpyrrolidone) catalyze Tsuji-Trost allylations in water with very high turnover numbers. The di-allylation of methylene active compounds and the allylation of bio-based phenols was performed in high yield. The allylation of lignin showed a high selectivity towards the phenolic OH groups.

Direct Synthesis of Diallyl Carbonate Via Urea Transesterification with Allyl Alcohol Over Metal Chlorides

A promising technique was studied towards diallyl carbonate (DAC) manufacture via urea transesterification with allyl alcohol over several metallic chlorides. It was revealed that the intermediate allyl carbamate (AC) was first generated via urea mono-alcoholysis with high yield, and subsequently AC further reacted with another allyl alcohol molecule to produce DAC. All the metal halides were evaluated for the overall reaction and the reaction of AC and allyl alcohol, respectively. This work found that the catalytic ability of catalysts originated from metal ions. Importantly, the highest yield of DAC could be achieved using LaCl3 as catalyst. In addition, the activation patterns of reactants were investigated using in situ FT-IR measurement. Based on the characterization results of X-ray power diffraction and elemental analysis of the lanthanum species, separated from the reaction conduced over LaCl3, a possible reaction mechanism was speculated. Graphical Abstract: [Figure not available: see fulltext.].

The design of efficient carbonate interchange reactions with catechol carbonate

Catechol carbonate (CC) has been investigated as an innovative and highly active reactant for carbonate interchange reactions (CIRs). Under mild conditions (atmospheric pressure, and 60-80°C), the selective synthesis of symmetric aliphatic carbonates (ROCO2R) has been achieved by the reaction of a slight excess of both primary and secondary alcohols with CC in the presence of NaOMe or MgO as a catalyst. Quantitative conversions have been reached in only 1 hour and products have been isolated in yields of up to 58% for dibutylcarbonate. Of note is that the reaction of glycerol with CC also proceeded under similar conditions (40-60°C, 1 atm) to afford glycerol carbonate (96-98%). The comparison of the reactivity of CC with that of conventional dialkyl carbonates, including dimethyl carbonate (DMC) and ethylene carbonate (EC), proved the superior performance of CC in all the investigated CIR processes. Accordingly, a mechanism has been formulated based on the leaving group ability of a catecholate anion originating from CC.