695-12-5

Basic information

• Product Name: VINYLCYCLOHEXANE
• Synonyms: VINYLCYCLOHEXANE;1-Vinylcyclohexane;Cyclohexane, vinyl-;cyclohexane,ethenyl-;Cyclohexane,ethenyl-(9CI);Cyclohexane,vinyl-;Cyclohexylethene;ethenyl-cyclohexan
• CAS NO: 695-12-5
• Molecular Formula: C₈H₁₄
• Molecular Weight: 110.2
• EINECS: 211-779-3
• Mol File: 695-12-5.mol
• Article Data: 69

Chemical Properties

• Melting Point: 121 °C
• Boiling Point: 128 °C(lit.)
• Flash Point: 70 °F
• Appearance: clear colourless liquid
• Density: 0.805 g/mL at 25 °C(lit.)
• Vapor Pressure: 13.8mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility: Insoluble in water.
• Stability: Light Sensitive
• BRN: 1304663
• CAS DataBase Reference: VINYLCYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: VINYLCYCLOHEXANE(695-12-5)
• EPA Substance Registry System: VINYLCYCLOHEXANE(695-12-5)

Safety Data

• Hazard Codes: F:Highly flammable
• Statements: 10
• Safety Statements: 16
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• RTECS: GV7800000
• F: 10
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 695-12-5(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Vinylcyclohexane is a useful reagent in cationic nickel(II)-catalyzed hydrosilylation of alkenes.

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 3652, 1967 DOI: 10.1021/ja00990a061The Journal of Organic Chemistry, 47, p. 1983, 1982 DOI: 10.1021/jo00349a038Synthesis, p. 446, 1979 DOI: 10.1055/s-1979-28713

Flammability and Explosibility

Flammable

InChI:InChI=1/C8H14/c1-2-8-6-4-3-5-7-8/h2,8H,1,3-7H2

Synthetic route

1-<2-trimethylsilyl)ethyl>cyclohexanol (81372-29-4) → vinylcyclohexane (695-12-5)

Conditions	Yield
With borontrifluoride acetic acid In dichloromethane at 25℃; for 0.0833333h;	95%

2-cyclohexylacetylene (931-48-6) → vinylcyclohexane (695-12-5)

Conditions	Yield
With hydrogen In hexane at 20℃; under 760.051 Torr; for 14h;	92%
With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; C19H13I2N3O2Ru; hydrogen In isopropyl alcohol at 80℃; under 3750.38 Torr; for 1h; Autoclave; Schlenk technique; chemoselective reaction;	89%
With hydrogen In toluene at 20℃; under 38002.6 Torr; for 12h; Autoclave; chemoselective reaction;	72%

(lithiomethyl)dimesitylborane + cyclohexanecarbaldehyde (2043-61-0) → vinylcyclohexane (695-12-5)

Conditions	Yield
With trifluoroacetic anhydride	76%

Methylenetriphenylphosphorane (19493-09-5) + cyclohexanecarbaldehyde (2043-61-0) → vinylcyclohexane (695-12-5) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
In tetrahydrofuran 1) 2 h, reflux, 2) 12 h, r.t.;	A 68% B n/a

C10H15O2P + cyclohexanecarbaldehyde (2043-61-0) → vinylcyclohexane (695-12-5)

Conditions	Yield
In 1,4-dioxane at 120℃; for 15h; Schlenk technique; Inert atmosphere;	65%

methyl trifluoromethanesulfonate (333-27-7) + cyclohexanecarbaldehyde (2043-61-0) → vinylcyclohexane (695-12-5)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In acetonitrile Wittig Olefination; Inert atmosphere; Glovebox; Electrochemical reaction;	57%

acetophenone (98-86-2) → styrene (292638-84-7) + vinylcyclohexane (695-12-5) + ethylbenzene (100-41-4)

Conditions	Yield
With sodium tetrahydroborate; hydrogen; nickel dichloride In isopropyl alcohol at 60 - 70℃; for 12h;	A 56% B 14% C 28%

vinylidenecyclohexane (5664-20-0) → vinylcyclohexane (695-12-5) + ethylidenecyclohexane (1003-64-1)

Conditions	Yield
Stage #1: vinylidenecyclohexane With triethylsilane; indium(III) chloride; triethyl borane In hexane; acetonitrile at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride; water In hexane; acetonitrile regioselective reaction;	A 10% B 32%
With water; diisobutylaluminium hydride 1.) hexane, 15 h, 25°C; 2.) 0°C; Multistep reaction;

cyclohexylmercury chloride (24371-94-6) + tri-n-butyl(vinyl)tin (7486-35-3) → vinylcyclohexane (695-12-5)

Conditions	Yield
In dimethyl sulfoxide Irradiation (UV/VIS); mixt. of substrate and mercurial is irradiated in nitrogen-purged solvent in Pyrex tube with 350-nm Rayonet photoreactor for 24 h; mixt. is poured into water, extd., extract is washed twice with aq. sodium thiosulfate, dried over anhyd. Na2SO4, concd.; (1)H-NMR;	8%

styrene (292638-84-7) → vinylcyclohexane (695-12-5) + ethyl-cyclohexane (1678-91-7) + ethylbenzene (100-41-4)

Conditions	Yield
With hydrogen; (η3-C3H5)Co[P(OMe)3]3 for 20.5h; Ambient temperature;	A 2.8% B 0.3% C 1.5%

cyclohexyl ethyl acetate (21722-83-8) → vinylcyclohexane (695-12-5)

Conditions	Yield
at 480℃;

1-cyclohexylethan-1-yl acetate (13487-27-9) → vinylcyclohexane (695-12-5) + ethylidenecyclohexane (1003-64-1)

Conditions	Yield
at 450℃;

(2-iodoethyl)cyclohexane (80203-35-6) → vinylcyclohexane (695-12-5)

Conditions	Yield
With quinoline

dithiocarbonic acid O-(1-cyclohexyl-ethyl ester)-S-methyl ester (99977-91-0) → vinylcyclohexane (695-12-5) + ethylidenecyclohexane (1003-64-1)

Conditions	Yield
at 250℃;

Cyclohexyloxirane (3483-39-4) → vinylcyclohexane (695-12-5) + rac-1-cyclohexylethanol (1193-81-3)

Conditions	Yield
With 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium 1) THF, -78 deg C, 5 min 2) MeOH, -78 deg C; Multistep reaction;

vinyl acetate (108-05-4) + cyclohexane (110-82-7) → vinylcyclohexane (695-12-5)

Conditions	Yield
	19 % Chromat.

2-cyclohexylacetylene (931-48-6) → vinylcyclohexane (695-12-5) + octane (111-65-9)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; 18-crown-6 ether; dihydrogen peroxide; sodium methylate 1.) THF, 65 deg C, 3 h, 2.) CH3OH, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

ethyl-cyclohexane (1678-91-7) → vinylcyclohexane (695-12-5) + 1-ethylcyclohexene (1453-24-3) + ethylidenecyclohexane (1003-64-1) + 4-ethylcyclohexene (3742-42-5, 75382-76-2) + 3-ethyl-1-cyclohexene (2808-71-1)

Conditions	Yield
trans-carbonylchlorobis(trimethylphosphine)rhodium under 50 Torr; for 72h; Mechanism; Irradiation;

(E)-cyclooctene (931-89-5) → (Z)-Cyclooctene (931-88-4, 931-87-3) + vinylcyclohexane (695-12-5) + 1,7-Octadiene (3710-30-3)

Conditions	Yield
at 512℃; Rate constant; further temperatures;

4-ethenylcyclohexene (100-40-3) → vinylcyclohexane (695-12-5)

Conditions	Yield
With η5-C9H11Fe(CO)2(isobutylene)+BF-; hydrogen; sodium iodide; palladium on activated charcoal Multistep reaction;

Di-(cyclohexyl)-n-butylboran (6917-84-6) + vinyl magnesium bromide (1826-67-1) → 1-hexene (592-41-6) + vinylcyclohexane (695-12-5)

Conditions	Yield
With iodine Product distribution; 1.) THF, room temperature, 1 h, 2.) THF, -78 deg C; other trialkylboranes;

2-chloro-1-cyclohexyl-1-ethanone (1892-09-7) → vinylcyclohexane (695-12-5)

Conditions	Yield
With lithium aluminium tetrahydride; aluminium trichloride; lithium 1.) Et2O, 2.) THF; Yield given. Multistep reaction;

2-cyclohexylpropanoic acid (6051-13-4) → vinylcyclohexane (695-12-5) + ethylidenecyclohexane (1003-64-1)

Conditions	Yield
With pyridine; lead(IV) acetate; copper diacetate In benzene for 4h; Heating;

cyclohexyl ethyl acetate (21722-83-8) → vinylcyclohexane (695-12-5) + acetic acid (64-19-7)

Conditions	Yield
at 400℃; Kinetics; Thermodynamic data; var. temp., pressure; ΔH(excit.);

rac-1-cyclohexylethanol (1193-81-3) → vinylcyclohexane (695-12-5) + ethylidenecyclohexane (1003-64-1)

Conditions	Yield
With dimethyl sulfoxide at 175℃; for 24h; Yield given. Yields of byproduct given;
5 % ruthenium on Al2O3; zirconium(IV) oxide at 376 - 398℃; Product distribution / selectivity;

trans,trans-4'-butyl<1,1'-bicyclohexyl>-4-carbonitrile (70784-10-0) + C16H20(2)H2O → vinylcyclohexane (695-12-5) + (1R,2R)-2-Cyclohexyl-1-phenyl-cyclobutanol + (1R,2S)-2-Cyclohexyl-1-phenyl-cyclobutanol + acetophenone (98-86-2)

Conditions	Yield
at 30℃; Product distribution; Irradiation; Norrish II photoreactivity; different solvents, different temperatures;

(2-cyclohexylidene-ethyl)dimethyl(phenyl)silane (79753-67-6) → vinylcyclohexane (695-12-5)

Conditions	Yield
With trifluoroacetic acid In tetrachloromethane for 20h; Ambient temperature;	95 % Spectr.

bicyclo<5.1.0>octan-2-one tosylhydrazone (73733-09-2) → vinylcyclohexane (695-12-5) + 1-octen-7-yne (65909-92-4) + bicyclo<4.2.0>oct-6-ene (37680-26-5)

Conditions	Yield
With sodium methylate at 160 - 170℃; under 0.5 Torr;	A 10 % Chromat. B 65 % Chromat. C 25 % Chromat.
With sodium methylate at 160 - 170℃; under 0.5 Torr; Mechanism; Product distribution;	A 10 % Chromat. B 65 % Chromat. C 25 % Chromat.

exo-7-chloromethylbicyclo<4.1.0>heptane (76200-08-3) → vinylcyclohexane (695-12-5) + exo-7-methylbicyclo<4.1.0>heptane (14135-43-4)

Conditions	Yield
With triphenylstannane In pentane at 25℃; for 24h; Irradiation; Yield given. Yields of byproduct given;
With triphenylstannane In pentane at 25℃; for 24h; Product distribution; Rate constant; Mechanism; Irradiation; several amount of reagent;

1-chloro-2-vinylcyclohexane → vinylcyclohexane (695-12-5)

Conditions	Yield
With triphenylstannane for 24h; Irradiation;

vinylcyclohexane (695-12-5) → 1-cyclohexylethane-1,2-diol (61414-09-3, 87858-06-8, 125874-67-1, 59411-58-4)

Conditions	Yield
With 4-methylmorpholine N-oxide In water; acetone at 20℃; for 3.5h; Inert atmosphere;	100%
Stage #1: vinylcyclohexane With sodium periodate; acetic acid; lithium bromide at 95℃; for 18h; Prevost-Woodward reaction; Stage #2: With potassium carbonate In methanol at 25℃; for 24h;	85%
With osmium(VIII) oxide; N-methyl-2-indolinone In water; acetone; acetonitrile Ambient temperature;	83%

vinylcyclohexane (695-12-5) → C8H14O

Conditions	Yield
With titanium(IV) isopropylate; Pentafluorobenzoic acid; C32H22F10N2O2; dihydrogen peroxide In water; 1,2-dichloro-ethane at 20℃; for 45h; Inert atmosphere; enantioselective reaction;	100%

vinylcyclohexane (695-12-5) → Cyclohexyloxirane (3483-39-4)

Conditions	Yield
With peracetic acid; C80H84Mn2N8O4*4ClO4(1-) In acetonitrile at 0℃; for 0.5h;	99%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 18h;	97%
With bis-trimethylsilanyl peroxide; rhenium(VII) oxide In dichloromethane for 7h;	95%

vinylcyclohexane (695-12-5) + benzoic acid (65-85-0) → 2-bromo-2-cyclohexylethyl benzoate (1403879-55-9)

Conditions	Yield
With N-bromophthalimide; 4-methylmorpholine N-oxide; sodium sulfate In dichloromethane at 20℃; for 22h; diastereoselective reaction;	99%
With N-Bromosuccinimide; 5,6-difluoro-2-(1-phenylethyl)benzo[d][1,2]selenazol-3(2H)-one In dichloromethane at 20℃; for 10h;	68%

vinylcyclohexane (695-12-5) + Dimethyl phosphite (868-85-9) → dimethyl (2-cyclohexylethyl)phosphonate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In neat (no solvent) for 0.5h; Solvent; UV-irradiation;	99%

vinylcyclohexane (695-12-5) → ethylidenecyclohexane (1003-64-1)

Conditions	Yield
bis(cyclopentadienyl)titanium dichloride; lithium aluminium tetrahydride at 180℃; for 2h;	98%
With sodium azide on γ-alumina at 20℃;
With [(dppb)Pt(C6F5)(H2O)]OTf In chloroform at 50℃; for 24h;	97 %Chromat.

vinylcyclohexane (695-12-5) + 1-(5,6-Dihydro-4H-pyran-2-yl)-2,2-dimethyl-propan-1-one → 1-[3-(2-Cyclohexyl-ethyl)-5,6-dihydro-4H-pyran-2-yl]-2,2-dimethyl-propan-1-one

Conditions	Yield
With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 135℃; for 12h;	98%

vinylcyclohexane (695-12-5) + phenylphosphinic acid (1779-48-2) → (2-cyclohexylethyl)(phenyl)phosphinic acid

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In water for 2h; Solvent; UV-irradiation; Green chemistry;	98%

vinylcyclohexane (695-12-5) + sodium benzenesulfonate (873-55-2) → ((2-cyclohexylethyl)sulfonyl)benzene (126002-58-2)

Conditions	Yield
With [Ir(dF(CF3)ppy)2(dtbbpy)]PF6; water; acetic acid In dichloromethane at 20℃; for 10h; Inert atmosphere; Irradiation; regioselective reaction;	98%

vinylcyclohexane (695-12-5) + (E)-1-phenyl-N-(1-phenylethylidene)methanamine (14428-98-9, 98325-59-8, 98359-08-1) → 1-[2-(2-cyclohexyl-ethyl)-phenyl]-ethanone

Conditions	Yield
Stage #1: vinylcyclohexane; (E)-1-phenyl-N-(1-phenylethylidene)methanamine With [RhCl(Ph3P)2] for 0.25h; microwave irradiation; Stage #2: Acid hydrolysis;	97%

vinylcyclohexane (695-12-5) + 4-methoxy-phenol (150-76-5) → 4-methoxy-2-(1-cyclohexylethyl)phenol (1173929-13-9)

Conditions	Yield
With decacarbonyldirhenium(0) In toluene at 150℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;	97%

vinylcyclohexane (695-12-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-cyclohexyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethane

Conditions	Yield
With (iPrPNN)CoCl2; sodium triethylborohydride In tetrahydrofuran; toluene at 25℃; for 0.25h; Inert atmosphere; Glovebox; Schlenk technique; chemoselective reaction;	97%
Stage #1: vinylcyclohexane; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With 6-di-tert-butylphosphinomethyl-2,2'-bipyridine In tetrahydrofuran for 0.0166667h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With sodium triethylborohydride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; Glovebox; Schlenk technique;	93%
With silver hexafluoroantimonate at 60℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere;	92%

vinylcyclohexane (695-12-5) + Diphenylphosphine oxide (4559-70-0) → (2-cyclohexylethyl)diphenylphosphine oxide

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In N,N-dimethyl-formamide for 2h; Solvent; UV-irradiation; Green chemistry;	97%

vinylcyclohexane (695-12-5) + ethyl 2,2-difluoro-2-iodoacetate (7648-30-8) → ethyl 4-cyclohexyl-2,2-difluoro-4-iodobutanoate

Conditions	Yield
With diethylzinc In hexane; acetonitrile at -20℃; for 16h; Schlenk technique; Inert atmosphere;	97%
With potassium carbonate In acetone at 20℃; for 16h; Schlenk technique; Inert atmosphere; Irradiation; Green chemistry;	96%
With potassium carbonate In acetone at 20℃; for 16h; Irradiation;	96%

vinylcyclohexane (695-12-5) + iodotrifluoromethane (2314-97-8) → C9H13F3

Conditions	Yield
With (dppf)Ni(o-tol)Cl; sodium t-butanolate In Hexafluorobenzene at 50℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;	97%

vinylcyclohexane (695-12-5) → (R)-1-cyclohexylethane-1,2-diol (59411-58-4, 61414-09-3, 125874-67-1, 87858-06-8)

Conditions	Yield
With methanesulfonamide; AD-mix β; water In ethanol at 4℃; for 24h; Sharpless Dihydroxylation;	96%
Stage #1: vinylcyclohexane With 2,2'-bis(1,3,2-benzodioxaborole); (bicyclo[2.2.1]hepta-2,5-diene)-(2,4-pentanedionato)rhodium (I); (S)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline In tetrahydrofuran at 20℃; for 6h; Stage #2: With sodium hydroxide; dihydrogen peroxide Product distribution / selectivity;	81%
Stage #1: vinylcyclohexane With 1,8-diazabicyclo[5.4.0]undec-7-ene; (2R,3S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4-diol; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; Sealed tube; Stage #2: With water; dihydrogen peroxide; sodium hydroxide at 0 - 20℃; for 4h; Inert atmosphere; Sealed tube; enantioselective reaction;	68%

vinylcyclohexane (695-12-5) + 2-pyridylmethyl formate (401515-97-7) → pyridin-2-ylmethyl 3-cyclohexylpropanoate

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; dodecacarbonyl-triangulo-triruthenium In N,N-dimethyl-formamide at 70℃; for 12h;	96%
With dodecacarbonyl-triangulo-triruthenium In N,N-dimethyl-formamide at 135℃; for 12h;	87%
With 1,3-bis(1-adamantyl)benzimidazoliumchloride, 1,3-dicyclohexylbenzimidazolium chloride; ruthenium(II) (norbanadiene)Cl2; potassium tert-butylate In tetrahydrofuran at 90℃; for 12h; Reagent/catalyst; Concentration; regioselective reaction;	87%

vinylcyclohexane (695-12-5) + Trichloroacetyl chloride (76-02-8) → 2,2-dichloro-3-(cyclohexyl)cyclobutanone (1029080-53-2)

Conditions	Yield
With copper; zinc; trichlorophosphate In diethyl ether at 40℃; for 2h;	96%
With zinc/copper couple; trichlorophosphate In diethyl ether Reflux;

vinylcyclohexane (695-12-5) + 6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione (1104636-73-8) → 2-(2-cyclohexylvinyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 24h; Inert atmosphere; stereoselective reaction;	96%

vinylcyclohexane (695-12-5) + 2,2-dimethyl-3,4-dihydro-2H-naphthalen-1-one (2977-45-9) → C20H28O

Conditions	Yield
With Fe(PMe3)4 at 70℃; for 20h; Inert atmosphere; regioselective reaction;	96%

vinylcyclohexane (695-12-5) → [1-chloro-2-(pentafluoro-λ6-sulfanyl)ethyl]cyclohexane (1263301-67-2)

Conditions	Yield
Stage #1: vinylcyclohexane With pentafluorosulfanyl chloride In dichloromethane at -40℃; Stage #2: With triethyl borane In hexane; dichloromethane at -40 - 20℃; Stage #3: With water; sodium hydrogencarbonate In hexane; dichloromethane	95%

[2,2]bipyridinyl (366-18-7) + vinylcyclohexane (695-12-5) → 3,3'-bis(2-cyclohexylethyl)-2,2'-bipyridine (1402856-01-2)

Conditions	Yield
With rhodium(III) acetylacetonate; 1,3-bis(mesityl)imidazolium chloride; sodium t-butanolate In toluene at 130℃; for 2h; regioselective reaction;	95%

vinylcyclohexane (695-12-5) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) → (3,3,4,4,5,5,6,6,6-nonafluoro-1-iodohexyl)cyclohexane (1464148-71-7)

Conditions	Yield
With tri-tert-butyl phosphine; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 12h; regioselective reaction;	95%
With sodium dithionite; C8ClF16O4S(1-)*C8H20N(1+); sodium hydrogencarbonate In water at 20℃; for 12h;	90%
With tri-tert-butyl phosphine In dichloromethane at 30℃; for 1h; Inert atmosphere; Irradiation; Sealed tube;	87%
With potassium carbonate In acetone at 20℃; for 16h; Schlenk technique; Inert atmosphere; Irradiation; Green chemistry;	79%
With tri-tert-butyl phosphine; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;

vinylcyclohexane (695-12-5) + diphenylsilane (775-12-2) → (2-cyclohexylethyl)diphenylsilane

Conditions	Yield
With sodium methylate In tetrahydrofuran Heating;	95%
With [(2-Ph2PC6H4)2PhSiCo(H)(Cl)(PMe3)] In neat (no solvent) at 70℃; for 30h; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere; regioselective reaction;	95%
With (1,3-diadamantylimidazol-2-ylidene)(PPh3)CoCl In toluene at 70℃; for 30h;	89%

vinylcyclohexane (695-12-5) → 1,2-dibromo-1-cyclohexylethane (81602-60-0)

Conditions	Yield
With bromine In chloroform at 0 - 20℃; for 1h; Inert atmosphere;	94%
With bromine
With bromine In tetrachloromethane
With bromine In dichloromethane at 0 - 5℃;
With urea hydrogen peroxide adduct; trifluoroacetic acid; lithium bromide at 100℃; for 1h;

vinylcyclohexane (695-12-5) + o-iodoacetanilide (19591-17-4) → 1-(3-cyclohexylindolin-1-yl)ethan-1-one

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; triethylamine; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In acetone at 35℃; for 48h; Heck Reaction; Inert atmosphere; Irradiation;	94%

vinylcyclohexane (695-12-5) + 2,3-dihydro-1H-benzo[b]silole → (S)-1-(2-cyclohexylethyl)-2,3-dihydro-1H-benzo[b]silole

Conditions	Yield
With C47H47N2O2Sc In benzene-d6 at 75℃; Schlenk technique; Sealed tube; enantioselective reaction;	94%

vinylcyclohexane (695-12-5) + N-(2-methylbenzoyl)-8-aminoquinoline (1182669-71-1) → 2-(2-cyclohexylethyl)-6-methyl-N-(quinolin-8-yl)benzamide

Conditions	Yield
With ortho-methylbenzoic acid; di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) In toluene at 160℃; for 12h; Sealed tube;	94%

vinylcyclohexane (695-12-5) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-4-cyclohexyl-butyric acid ethyl ester

Conditions	Yield
With pyridine; Eosin Y; 1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate at 23℃; for 14h; Inert atmosphere; Sealed tube; Irradiation;	93%
With dibenzoyl peroxide (heating);

Upstream product

• 3483-39-4 Cyclohexyloxirane 
• 106-99-0 buta-1,3-diene 
• 2043-61-0 cyclohexanecarbaldehyde 
• 80203-35-6 (2-iodoethyl)cyclohexane 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 24371-94-6 cyclohexylmercury chloride 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 76200-08-3 exo-7-chloromethylbicyclo<4.1.0>heptane 
• 81372-29-4 1-<2-trimethylsilyl)ethyl>cyclohexanol 
• 73733-09-2 bicyclo<5.1.0>octan-2-one tosylhydrazone 
• 79753-67-6 (2-cyclohexylidene-ethyl)dimethyl(phenyl)silane 
• 70784-10-0 trans,trans-4'-butyl<1,1'-bicyclohexyl>-4-carbonitrile 
• 1193-81-3 rac-1-cyclohexylethanol 

Downstream Products

• 100314-83-8 trans-2-cyclohexyl-cyclopropanecarboxylic acid ethyl ester 
• 28239-43-2 Trichloro-1,1,1-cyclohexyl-3-propan 
• 7087-57-2 2,2-Dibrom-1-cyclohexyl-cyclopropan 
• 7077-71-6 2-(2-cyclohexyl-ethyl)-octanoic acid 
• 1940-19-8 1-vinylcyclohexanol 
• 4065-85-4 1-Hydroperoxy-1-vinylcyclohexan 
• 4442-79-9 cyclohexylethan-1-ol 
• 30011-03-1 N,N-Dimethyl-(2-chlorcyclohexyl-oxymethylen)-immoniumchlorid 
• 699432-73-0 (2S,3aS,6S)-6-tert-butyl-2-cyclohexyl-5-methyl-tetrahydroimidazo[1,5-b]isoxazol-4-one 
• 911834-88-3 (E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-9,19-dien-3-yn-5-one 
• 17343-88-3 (E)-3-cyclohexyl-acrylic acid ethyl ester 
• 544459-32-7 N-(2-pyridyl)-3-cyclohexyl propanamide 

Relevant articles and documents

Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydroboration and Dehydroboration

We report a dehydroboration process that can be coupled with chain-walking hydroboration to create a one-pot, contra-thermodynamic, short-or long-range isomerization of internal olefins to terminal olefins. This dehydroboration occurs by a sequence comprising activation with a nucleophile, iodination, and base-promoted elimination. The isomerization proceeds at room temperature without the need for a fluoride base, and the substrate scope of this isomerization is expanded over those of previous isomerizations we have reported with silanes.

Norrish type II reactions of acyl azolium salts

The photochemical reactivity of acyl azolium salts derived from aliphatic carboxylic acids has been investigated. These species, which serve as models for intermediates generated in N-heterocyclic carbene (NHC) organocatalysis, undergo Norrish type II elimination reactions under irradiation with UVA light in analogy to structurally related aromatic ketones. Moreover, efficient Norrish-Yang cyclization was observed from an adamantyl-substituted derivative. These results further demonstrate the ability of NHCs to influence the absorption properties and photochemical reactivity of carbonyl groups during a catalytic cycle.

A Systems Approach to a One-Pot Electrochemical Wittig Olefination Avoiding the Use of Chemical Reductant or Sacrificial Electrode

An unprecedented one-pot fully electrochemically driven Wittig olefination reaction system without employing a chemical reductant or sacrificial electrode material to regenerate triphenylphosphine (TPP) from triphenylphosphine oxide (TPPO) and base-free in situ formation of Wittig ylides, is reported. Starting from TPPO, the initial step of the phosphoryl P=O bond activation proceeds through alkylation with RX (R=Me, Et; X=OSO2CF3 (OTf)), affording the corresponding [Ph3POR]+X? salts which undergo efficient electroreduction to TPP in the presence of a substoichiometric amount of the Sc(OTf)3 Lewis acid on a Ag-electrode. Subsequent alkylation of TPP affords Ph3PR+ which enables a facile and efficient electrochemical in situ formation of the corresponding Wittig ylide under base-free condition and their direct use for the olefination of various carbonyl compounds. The mechanism and, in particular, the intriguing role of Sc3+ as mediator in the TPPO electroreduction been uncovered by density functional theory calculations.