2039-93-2

Basic information

• Product Name: 2-Phenyl-1-butene
• Synonyms: a-Ethylstyrene;Styrene, a-ethyl- (7CI,8CI)
• CAS NO: 2039-93-2
• Molecular Formula: C₁₀H₁₂
• Molecular Weight: 132.20
• EINECS: 248-846-1
• Mol File: 2039-93-2.mol
• Article Data: 75

Chemical Properties

• Boiling Point: 184.8 °C at 760 mmHg
• Flash Point: 57.1 °C
• Appearance: /
• Density: 0.871 g/cm³
• Vapor Pressure: 0.986mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: 2-Phenyl-1-butene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-1-butene(2039-93-2)
• EPA Substance Registry System: 2-Phenyl-1-butene(2039-93-2)

Safety Data

• Hazardous Substances Data: 2039-93-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12/c1-3-9(2)10-7-5-4-6-8-10/h4-8H,2-3H2,1H3

Synthetic route

ethylmagnesium bromide (925-90-6) + phenylacetylene (536-74-3) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
With copper(I) bromide; lithium bromide In tetrahydrofuran at -60℃; for 1h;	98%

Methyltriphenylphosphonium bromide (1779-49-3) + 1-phenyl-propan-1-one (93-55-0) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Wittig Olefination; Inert atmosphere; Stage #2: 1-phenyl-propan-1-one In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	97%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Schlenk technique; Stage #2: 1-phenyl-propan-1-one In tetrahydrofuran at 0 - 20℃;	90%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 1-phenyl-propan-1-one In tetrahydrofuran at 20℃; Inert atmosphere;	87%

bromobenzene (108-86-1) + but-1-en-2-ylboronic acid → 1-ethylstyrene (2039-93-2)

Conditions	Yield
With cis,cis,cis-tetrakis[(diphenylphosphanyl)methyl]cyclopentane; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 80℃; for 20h; Suzuki reaction;	91%

β-phenylisovaleryl peroxide (62726-47-0) → 4,4-dimethyl-2-oxo-chroman (29598-22-9) + 2-methyl-1-phenyl-2-propene (3290-53-7) + (2-methyl-1-propenyl)-benzene (768-49-0) + 1-ethylstyrene (2039-93-2) + 3-methyl-3-phenylbutanoic acid (1010-48-6) + 3-Methyl-3-phenyl-butyric acid 1,1-dimethyl-2-phenyl-ethyl ester (62698-31-1)

Conditions	Yield
With P1 silica Product distribution; Rate constant; CH3CN as a solvent, other temperature, possible ways of the products formation;	A 7.73 % Chromat. B 35.5 % Chromat. C 4.2 % Chromat. D 3.78 % Chromat. E 87% F 6.21 % Chromat.

methylenetriphenylarsorane (47025-43-4, 19365-61-8) + 1-bromopropylbenzene (2114-36-5, 101308-38-7) → 1-propenylbenzene (873-66-5) + 1-ethylstyrene (2039-93-2)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane for 1h; Ambient temperature;	A 85% B 13%

2-phenyl-2-butanol (1565-75-9, 19641-57-7) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
With acetic anhydride; magnesium bromide In dichloromethane at 20℃; for 5h; Dehydration;	83%

1-phenyl-eth-1-en-1-yl diphenyl phosphate (50523-12-1) + triethylaluminum (97-93-8) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) at 25℃; for 2h;	80%
With tetrakis(triphenylphosphine) palladium(0) In hexane; 1,2-dichloro-ethane at 25℃; for 2h;	80%

(trimethylstannyl)methyl-lithium (76373-10-9) + (CH3)2C4H9SnCH2Li (94083-30-4) + 1-phenyl-propan-1-one (93-55-0) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
	78%

(trimethylstannyl)methyl-lithium (76373-10-9) + 1-phenyl-propan-1-one (93-55-0) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
	78%

iodobenzene (591-50-4) + but-1-en-2-ylboronic acid → 1-ethylstyrene (2039-93-2)

Conditions	Yield
With cis,cis,cis-tetrakis[(diphenylphosphanyl)methyl]cyclopentane; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki reaction;	78%

trimethylsulphonium iodide (2181-42-2) + 1-bromopropylbenzene (2114-36-5, 101308-38-7) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
With n-butyllithium; lithium iodide In tetrahydrofuran; hexane from 0 degC to room temp.;	72%

Methyltriphenylphosphonium bromide (1779-49-3) + propionaldehyde (123-38-6) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.0833333h; Stage #2: propionaldehyde In tetrahydrofuran; hexane at 0℃; for 14h;	64%

[Pd(CH2CMe2Ph)(κ3-N,N′,N′′-(N,N-bis(pyrid-2-ylmethyl)-N-(3-hydroxypropyl)amine))][HCO3] → tert-butylbenzene (253185-03-4, 253185-04-5) + 2-methyl-1-phenyl-2-propene (3290-53-7) + 2-Methyl-1-phenyl-2-propanol (100-86-7) + 1-ethylstyrene (2039-93-2) + (E)-2-phenyl-2-butene (768-00-3) + 2-phenyl-2-butanol (1565-75-9, 19641-57-7)

Conditions	Yield
With dihydrogen peroxide In water; water-d2 for 0.05h;	A 6% B 4% C 10% D 5% E 9% F 51%

dimethylsulfone (67-71-0) + 1-Phenyl-1-propanol (93-54-9) → 1-ethylstyrene (2039-93-2) + hydrogen (1333-74-0)

Conditions	Yield
With 1,10-Phenanthroline; potassium tert-butylate; iron(II) chloride In toluene at 120℃; for 8h; Julia Olefin Synthesis; Inert atmosphere; Schlenk technique;	A 50% B n/a

methyl-triphenylphosphonium iodide (2065-66-9) + 1-phenyl-propan-1-one (93-55-0) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane Wittig reaction; Inert atmosphere; Cooling with ice;	40.6%
With potassium tert-butylate In diethyl ether at 20℃; for 4h; Wittig olefination;
With potassium tert-butylate In tetrahydrofuran Wittig Olefination;
Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: 1-phenyl-propan-1-one In tetrahydrofuran Inert atmosphere;

1-phenyl-propan-1-one (93-55-0) + H2C=TiCl2 (79899-81-3) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
Stage #1: 1-phenyl-propan-1-one; H2C=TiCl2 In diethyl ether; toluene at -40 - 20℃; Stage #2: With water	38%

2-phenyl-2-butanol (1565-75-9, 19641-57-7) + acetic anhydride (108-24-7) → 1-ethylstyrene (2039-93-2) + (E)-2-phenyl-2-butene (768-00-3) + 2-phenylbutan-2-yl acetate (10042-36-1) + dimethylglyoxal (431-03-8)

Conditions	Yield
With cobalt(II) chloride In acetonitrile at 50℃; for 8h; Yields of byproduct given;	A n/a B n/a C 31% D n/a

2-phenylbutan-1-ol (2035-94-1) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
With infusorial earht at 300 - 400℃; bei der Destillation;
With potassium hydroxide Destillation;

sec-Butylbenzene (135-98-8, 36383-15-0) → 1-ethylstyrene (2039-93-2) + 2-phenylbut-2-ene (767-99-7, 768-00-3, 2082-61-3)

Conditions	Yield
With chromium(III) oxide at 600℃;

3-phenyl-pent-3-enoic acid (87931-48-4) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
With sulfuric acid

ethylmagnesium bromide (925-90-6) + phenylacetylene (536-74-3) → (E)-hex-3-en-3-ylbenzene (39857-50-6) + 1-ethylstyrene (2039-93-2) + Diphenyl-3,6-oktadien-3,5, E,E (54068-73-4)

Conditions	Yield
(i) CuBr, Et2O, (ii) /BRN= 605461/, pentane, (iii) aq. HCl; Multistep reaction;

ethylmagnesium bromide (925-90-6) + phenylacetylene (536-74-3) → 1-ethylstyrene (2039-93-2) + Diphenyl-3,6-oktadien-3,5, E,E (54068-73-4) + dodeca-3c,5c,7c,9c-tetraene (31699-39-5)

Conditions	Yield
(i) CuBr, Et2O, (ii) /BRN= 605461/, pentane, (iii) aq. HCl; Multistep reaction;

sec-Butylbenzene (135-98-8, 36383-15-0) → 1-ethylstyrene (2039-93-2) + (Z)-2-phenylbut-2-ene (767-99-7) + (1-chloro-2-butanyl)benzene (64343-08-4) + (3-chloro-1-methyl-propyl)-benzene (13556-61-1) + erythro-2-chloro-3-phenylbutane (5706-90-1, 5706-91-2, 27059-45-6) + threo-2-chloro-3-phenylbutane (5706-90-1, 5706-91-2, 27059-45-6)

Conditions	Yield
at 25℃; Product distribution; chlorination; phase and solvent influence on the relative selectivity;

1-diazo-2-methyl-2-phenylpropane → 2-methyl-1-phenyl-2-propene (3290-53-7) + (2-methyl-1-propenyl)-benzene (768-49-0) + 1-ethylstyrene (2039-93-2) + (1-methylcyclopropyl)benzene (2214-14-4) + (Z)-2-phenylbut-2-ene (767-99-7) + (E)-2-phenyl-2-butene (768-00-3)

Conditions	Yield
In decalin at 180℃; for 0.0833333h; Mechanism; Product distribution; other reaction conditions were investigated;

1-diazo-2-methyl-2-phenylpropane → (2-methyl-1-propenyl)-benzene (768-49-0) + 1-ethylstyrene (2039-93-2) + (1-methylcyclopropyl)benzene (2214-14-4) + (E)-2-phenyl-2-butene (768-00-3)

Conditions	Yield
In pentane Ambient temperature; Irradiation; Further byproducts given. Yields of byproduct given;

2-phenyl-2-butanol (1565-75-9, 19641-57-7) → 1-ethylstyrene (2039-93-2) + (Z)-2-phenylbut-2-ene (767-99-7) + (E)-2-phenyl-2-butene (768-00-3)

Conditions	Yield
With sulfuric acid at 60℃; for 2h;
With sulfuric acid
With potassium hydrogensulfate; 4-tert-Butylcatechol at 200℃; for 2h; Overall yield = 71 %; Overall yield = 1.87 mg;

2-phenyl-2-butanol (1565-75-9, 19641-57-7) → 1-ethylstyrene (2039-93-2) + (E)-2-phenyl-2-butene (768-00-3) + 2-phenylbutan-2-yl acetate (10042-36-1) + dimethylglyoxal (431-03-8)

Conditions	Yield
With acetic anhydride; cobalt(II) chloride In acetonitrile at 50℃; for 8h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

3-(2-phenyl-2-propyl)diazirine (82518-02-3) → (2-methyl-1-propenyl)-benzene (768-49-0) + 1-ethylstyrene (2039-93-2) + (1-methylcyclopropyl)benzene (2214-14-4) + (E)-2-phenyl-2-butene (768-00-3)

Conditions	Yield
In benzene Ambient temperature; Irradiation; Further byproducts given. Yields of byproduct given;

2-methyl-2-phenylpropanal p-tosylhydrazone → 2-methyl-1-phenyl-2-propene (3290-53-7) + (2-methyl-1-propenyl)-benzene (768-49-0) + 1-ethylstyrene (2039-93-2) + (E)-2-phenyl-2-butene (768-00-3)

Conditions	Yield
With lithium methanolate In various solvent(s) at 80℃; for 5h; Yield given. Further byproducts given. Yields of byproduct given;

phenylmagnesium bromide + 1-chlorobutan-2-one (616-27-3) → 1-ethylstyrene (2039-93-2)

Conditions	Yield
With lithium; magnesium bromide 1.) Et2O, 2.) THF; Yield given. Multistep reaction;

ethene (74-85-1) + 1-ethylstyrene (2039-93-2) → (R)-(-)-3-methyl-3-phenyl-1-pentene (768392-48-9)

Conditions	Yield
With bi(allylnickel bromide); C39H30NO2P; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at -78℃; for 1.01667h; optical yield given as %ee; enantioselective reaction;	99%
With [(R)-1,1'-binaphthyl-2,2'-diyldioxy]{bis[(S)-(1-phenylethyl)]amino}phosphine; bi(allylnickel bromide); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane under 760.051 Torr; for 4h; Inert atmosphere; Cooling with acetone-dry ice; optical yield given as %ee; enantioselective reaction;	99.7%
Stage #1: ethene With bi(allylnickel bromide); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine In dichloromethane at -70℃; under 760.051 Torr; Schlenk technique; Inert atmosphere; Glovebox; Stage #2: 1-ethylstyrene In dichloromethane at -70 - -65℃; under 760.051 Torr; for 4h; Inert atmosphere;	99%
With bi(allylnickel bromide); {benzyl[(S)-1-(1-naphthyl)ethyl]amino}[(R)-1,1'-binaphthyl-2,2'-diyldioxy]phosphine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at -78℃; for 4h; Inert atmosphere; enantioselective reaction;

1-ethylstyrene (2039-93-2) → sec-Butylbenzene (135-98-8, 36383-15-0)

Conditions	Yield
With hydrogen; {Ir(cod)[2-methyl-4-((S)-2-Ph2P-ethyl)oxazoline]}*BARF In dichloromethane at 25℃; under 37503.8 Torr; for 2h;	99%
With hydridotetracarbonylcobalt; carbon monoxide In dichloromethane at 0℃; Rate constant;
With Ni(mesal)2; sulfuric acid; N-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]-N,N-dimethylamine; triisobutylaluminum 1.) at room temp., 30 h; Yield given. Multistep reaction;

Bromoform (75-25-2) + 1-ethylstyrene (2039-93-2) → 2,2-dibromo-1-ethyl-1-phenylcyclopropane (66444-06-2)

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In dichloromethane; water at 5℃;	99%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 20 - 60℃; Inert atmosphere;	80%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 20 - 60℃; Inert atmosphere;	80%

1-ethylstyrene (2039-93-2) → 2-Phenyl-1-azidobutan-2-ol

Conditions	Yield
Stage #1: 1-ethylstyrene With trimethylsilylazide; 9-(2-mesityl)-10-methylacridinium perchlorate In toluene at 20℃; for 4h; Irradiation; Stage #2: With hydrogenchloride; triphenylphosphine In water; acetonitrile at 20℃; for 0.5h;	99%

1-ethylstyrene (2039-93-2) + 1-cyclopropyl-3-(3,5-dimethylphenyl)urea (64392-97-8) → C22H28N2O + C22H28N2O

Conditions	Yield
With C42H34F10IrN4(1+)*C110H140BN2O12(1-) In dichloromethane at -20℃; for 24h; Inert atmosphere; Photolysis; enantioselective reaction;	A 98% B n/a

1-ethylstyrene (2039-93-2) → 2-phenylbut-2-ene (767-99-7, 768-00-3, 2082-61-3)

Conditions	Yield
With borane-ammonia complex; (3aR,7aR)-1,3-diisopropyl-2-((2-((E)-(quinolin-2-ylmethylene)amino)phenyl)amino)octahydro-1H-benzo[d][1,3,2]diazaphosphole 2-oxide; cobalt(II) bromide; sodium t-butanolate In toluene at 60℃; for 12h; Reagent/catalyst; Solvent; Glovebox; Inert atmosphere;	96%

1-ethylstyrene (2039-93-2) → (E)-2-phenyl-2-butene (768-00-3)

Conditions	Yield
With borane-ammonia complex; (3aR,7aR)-1,3-diisopropyl-2-((2-((E)-(pyridin-2-ylmethylene)amino)phenyl)amino)octahydro-1H-benzo[d][1,3,2]diazaphosphole 2-oxide; cobalt(II) bromide; sodium t-butanolate In toluene at 60℃; for 12h; Reagent/catalyst; Glovebox; Inert atmosphere; Large scale; stereoselective reaction;	95%
With (PPO)FeCl2; sodium triethylborohydride In tetrahydrofuran; pentane at 20℃; for 2h; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique; stereoselective reaction;	92%
With aluminium(III) triflate In 1,2-dichloro-ethane at 20℃; for 12h; Reagent/catalyst; Solvent; Inert atmosphere; stereoselective reaction;	82%
With C21H35N3PRu*F6P(1-) In [(2)H6]acetone at 70℃; for 29h; Inert atmosphere; stereoselective reaction;
With C22H27Cl2CoN3S; sodium triethylborohydride In neat (no solvent) at 20℃; for 1h; Schlenk technique; Glovebox; stereoselective reaction;	n/a

1-ethylstyrene (2039-93-2) → 1-Bromo-2-fluoro-2-phenylbutane (180347-97-1)

Conditions	Yield
With N-Bromosuccinimide; triethylamine tris(hydrogen fluoride) In dichloromethane at 0 - 20℃; for 14.25h; regioselective reaction;	94%
With N-Bromosuccinimide; triethylamine tris(hydrogen fluoride) In dichloromethane 1.) 0 deg C, 15 min, 2.) r.t., 12 h; Yield given;

diazoacetic acid ethyl ester (623-73-4) + 1-ethylstyrene (2039-93-2) → ethyl (1R,2R)-2-ethyl-2-phenylcyclopropanecarboxylate (1620152-21-7)

Conditions	Yield
With C32H42CoN2O4; potassium thioacetate In dichloromethane at 20℃; for 32h; enantioselective reaction;	94%

1-ethylstyrene (2039-93-2) + N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide (1150-26-1) → C24H25NO3S

Conditions	Yield
With [n-Bu4N][BF4]; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane; acetonitrile at 20℃; for 2h; Electrolysis; Inert atmosphere; Electrochemical reaction; regioselective reaction;	93%

1-ethylstyrene (2039-93-2) + 2,2-difluoro-1-phenyl-1-trimethylsiloxyethene (86340-78-5) → C18H18F2O

Conditions	Yield
With perchloric acid In water at 50℃; for 15h;	92%

1-ethylstyrene (2039-93-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (R)-(+)-4,4,5,5-tetramethyl-2-(2-phenylbutyl)-1,3,2-dioxaborolane (1325729-42-7)

Conditions	Yield
With C26H36CoN3O In tetrahydrofuran at 25℃; for 3h; Inert atmosphere; Glovebox; enantioselective reaction;	91%
With C29H33Cl2FeN3O; sodium triethylborohydride In tetrahydrofuran; diethyl ether at 0℃; for 1h; Inert atmosphere; Schlenk technique; enantioselective reaction;	91%

1-ethylstyrene (2039-93-2) + [2,2-Difluoro-1-(4-methoxy-phenyl)-vinyloxy]-trimethyl-silane (210302-61-7) → C19H20F2O2

Conditions	Yield
With aluminum (III) chloride In fluorobenzene at 45℃; for 2h;	91%

1-ethylstyrene (2039-93-2) + acetylacetone (123-54-6) → 3-acetyl-5-ethyl-2-methyl-5-phenyl-4,5-dihydrofuran (134391-07-4)

Conditions	Yield
With CeONO2 (CAN) In acetonitrile at 20℃; for 0.0833333h; Mechanism; Rate constant; other solvent (MeOH);	90%
With CeONO2 (CAN) In acetonitrile at 20℃; for 0.0833333h; or in MeOH;	90%

1-ethylstyrene (2039-93-2) + bis(pinacol)diborane (73183-34-3) → (R)-(+)-4,4,5,5-tetramethyl-2-(2-phenylbutyl)-1,3,2-dioxaborolane (1325729-42-7)

Conditions	Yield
Stage #1: bis(pinacol)diborane With C34H28N2O3S; copper(l) chloride; sodium t-butanolate In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: 1-ethylstyrene With methanol In tetrahydrofuran at -15℃; for 48h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	90%
With CuCl; C3H2N2Ph2(C6H3MePh)(C6H4SO3); NaOtBu In tetrahydrofuran; methanol -15°C; 48 h;	90%

1-ethylstyrene (2039-93-2) + diphenylsilane (775-12-2) → (S)-(-)-diphenyl(2-phenylbutyl)silane

Conditions	Yield
With C25H33Cl2FeN3O; sodium triethylborohydride In tetrahydrofuran; toluene at 20℃; for 12h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Cooling with ice; stereoselective reaction;	90%

carbon monoxide (201230-82-2) + 1-ethylstyrene (2039-93-2) → (3S)-3-Phenylpentanal (27855-02-3)

Conditions	Yield
With (acetylacetonato)dicarbonylrhodium (l); (S,S)-YanPhos; hydrogen In toluene at 80℃; under 3750.38 Torr; for 48h; Autoclave; enantioselective reaction;	90%

1-ethylstyrene (2039-93-2) + ((2,2-difluoro-1-phenylvinyl)oxy)triethylsilane → C18H18F2O

Conditions	Yield
With indium(III) chloride In tetrahydrofuran at 25℃; for 20h;	90%

1-ethylstyrene (2039-93-2) → (E)-(1-nitrobut-1-en-2-yl)benzene (119880-58-9, 149893-90-3, 149893-89-0)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; silver nitrate In 1,2-dichloro-ethane at 70℃; for 12h; Molecular sieve;	88%
With ammonium cerium (IV) nitrate; acetic acid; sodium nitrite In chloroform Sealed tube; Sonication;	48%
With ammonium cerium (IV) nitrate; acetic acid; sodium nitrite In chloroform for 6h; Inert atmosphere; Sealed tube; Sonication;	40%

1-ethylstyrene (2039-93-2) → 1-phenyl-propan-1-one (93-55-0)

Conditions	Yield
With monoethylene glycol diethyl ether at 90℃; for 12h; Green chemistry;	88%
With tetrahydrofuran; oxygen In water at 20℃; for 18h; Irradiation; Green chemistry;	85%
With N-hydroxyphthalimide; oxygen In N,N-dimethyl acetamide; water at 80℃; for 72h;	57 %Chromat.

1-ethylstyrene (2039-93-2) + bis(p-toluenesulfonyl) sulfur diimide (851-06-9) → N1,N2-Ditosyl-2-phenyl-2-buten-sulfinamidin (74608-16-5)

Conditions	Yield
In tetrachloromethane at 20℃; for 14h;	86%

1-ethylstyrene (2039-93-2) → benzyl ethyl ketone (1007-32-5)

Conditions	Yield
With [hydroxy(tosyloxy)iodo]benzene In methanol at 20℃; for 0.333333h;	86%
With oxone; sodium iodide In water; acetonitrile at 20℃; for 15h; Green chemistry;	72%

1-ethylstyrene (2039-93-2) + p-nitrobenzenesulfonamide (6325-93-5) → C16H16N2O4S

Conditions	Yield
With [bis(acetoxy)iodo]benzene; tricyclohexylphosphine selenide In dichloromethane Inert atmosphere; Sealed tube; regioselective reaction;	86%

1-ethylstyrene (2039-93-2) + bis(p-toluenesulfonyl) sulfur diimide (851-06-9) → N-(1-Methyl-2-phenylallyl)-N-(p-toluolsulfonamidothio)-p-toluolsulfonamid (74607-99-1)

Conditions	Yield
In toluene 1) 20 deg C, 7 h; 2) 50 deg C, 0.5 h;	85%

Upstream product

• 87931-48-4 3-phenyl-pent-3-enoic acid 
• 47025-43-4 methylenetriphenylarsorane 
• 2114-36-5 1-bromopropylbenzene 
• 93-55-0 1-phenyl-propan-1-one 
• 108-86-1 bromobenzene 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 67-71-0 dimethylsulfone 
• 93-54-9 1-Phenyl-1-propanol 
• 768-00-3 (E)-2-phenyl-2-butene 
• 3805-10-5 2,2-(dimethyl)-2-phenylacetaldehyde 
• 1052762-47-6 lithium 1-phenylethenolate 
• 98-86-2 acetophenone 
• 137744-15-1 CH₂Cl₂Zr 

Downstream Products

• 86766-10-1 (3R,5R)-3-Ethyl-3,5-diphenyl-[1,2]dioxolane 
• 86766-09-8 (3R,5S)-3-Ethyl-3,5-diphenyl-[1,2]dioxolane 
• 112778-36-6 (3-Difluoromethylene-1-ethyl-cyclobutyl)-benzene 
• 112778-29-7 (1-Ethyl-2,2-difluoro-3-methylene-cyclobutyl)-benzene 
• 74608-16-5 N¹,N²-Ditosyl-2-phenyl-2-buten-sulfinamidin 
• 74607-99-1 N-(1-Methyl-2-phenylallyl)-N-(p-toluolsulfonamidothio)-p-toluolsulfonamid 
• 5787-28-0 (S)-2-phenyl-1-butane 
• 27998-43-2 2,2-Dichlor-1-ethyl-1-phenyl-cyclopropan 
• 66444-06-2 2,2-dibromo-1-ethyl-1-phenylcyclopropane 
• 180347-97-1 1-Bromo-2-fluoro-2-phenylbutane 
• 180348-11-2 1-Bromo-2-phenylbutan-2-ol 
• 2404-42-4 (S)-(-)-2-phenyl-butane-1,2-diol 
• 93-55-0 1-phenyl-propan-1-one 
• 1007-32-5 benzyl ethyl ketone 

Relevant articles and documents

STRUCTURES OF ISOMERIC ANIONS IN THE GAS PHASE: ARYLLALLYL AND ARYLCYCLOPROPYL ANIONS.

The isomeric 1-phenylcyclopropyl and 2-phenylallyl anions have been prepared in the gas phase by proton-abstraction reactions. They have been shown to be distinct, noninterconverting species by their differing reactions with D//2O, O//2, and N//2O. The 2-methyl-1-phenylcyclopropyl and 1-methyl-2-phenylallyl anions are also shown to react differently with these reagents. However, in the presence of H//2O the 1-methyl-2-phenylallyl anion is converted to the 1-methyl-1-phenylallyl anion by proton addition and reabstraction. The utility of these and other reagents for determining ion structure in the gas phase is discussed.

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

Iron-Catalyzed Direct Julia-Type Olefination of Alcohols

Herein, we report an iron-catalyzed, convenient, and expedient strategy for the synthesis of styrene and naphthalene derivatives with the liberation of dihydrogen. The use of a catalyst derived from an earth-abundant metal provides a sustainable strategy to olefins. This method exhibits wide substrate scope (primary and secondary alcohols) functional group tolerance (amino, nitro, halo, alkoxy, thiomethoxy, and S- A nd N-heterocyclic compounds) that can be scaled up. The unprecedented synthesis of 1-methyl naphthalenes proceeds via tandem methenylation/double dehydrogenation. Mechanistic study shows that the cleavage of the C-H bond of alcohol is the rate-determining step.