34143-74-3

Basic information

• Product Name: 1H,1H,2H,2H-PERFLUORODECANETHIOL
• Synonyms: 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORO-1-DECANETHIOL;1H,1H,2H,2H-PERFLUORODECANE-1-THIOL;1H,1H,2H,2H-PERFLUORODECANETHIOL;1H,1H,2H,2H-PERFLUORODECYL-1-THIOL;1H,1H,2H,2H-PERFLUORO-1-DECANETHIOL;1H,1H,2H,2H-Perfluorodecanethiol 99%;1H,1H,2H,2H-Perfluorodecanethiol99%;3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluoro-1-decanethiol, 1H,1H,2H,2H-Perfluoro-1-decanethiol
• CAS NO: 34143-74-3
• Molecular Formula: C₁₀H₅F₁₇S
• Molecular Weight: 480.18
• Mol File: 34143-74-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 15 °C
• Boiling Point: 82 °C
• Flash Point: >230 °F
• Appearance: /
• Density: 1.678 g/mL at 25 °C
• Vapor Pressure: 0.482mmHg at 25°C
• Refractive Index: n20/D 1.333
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.61±0.10(Predicted)
• CAS DataBase Reference: 1H,1H,2H,2H-PERFLUORODECANETHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1H,1H,2H,2H-PERFLUORODECANETHIOL(34143-74-3)
• EPA Substance Registry System: 1H,1H,2H,2H-PERFLUORODECANETHIOL(34143-74-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 34143-74-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 34143-74-3 differently. You can refer to the following data:
1. 1H, 1H, 2H, 2H-perfluorododecyl mercaptan is a perfluorinated organic substance and can be used as an organic reagent.
2. PFDT can be used to modify the surface of polydopamine-silver (Ag) nanoparticle array for surface enhanced raman scattering detection. It can also be used as an anti-corrosive coating that blocks oxidation and gives lubricating properties on the surface of copper. SAMs based on PFDT with a high water contact angle of 120° and a work function of 5.44 eV were coated on gold (Au) electrodes which were used in the fabrication of N and P-typed organic thin film transistors.

General Description

1H,1H,2H,2H-Perfluorodecanethiol (PFDT) is a fluoro-organothiol that provides a hydrophobic surface coating by forming a self-assemble monolayer (SAM) that increases the wettability and lowers the surface energy.

InChI:InChI=1/C10H5F17S/c11-3(12,1-2-28)4(13,14)5(15,16)6(17,18)7(19,20)8(21,22)9(23,24)10(25,26)27/h28H,1-2H2

Synthetic route

1,2-bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)disulfide (42977-21-9) → 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3)

Conditions	Yield
With tributylphosphine; water In tetrahydrofuran at 20℃; for 9h; Inert atmosphere;	70%

S-[2-(perfluorooctyl)ethyl]thioacetate (125640-21-3) → 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + 1,2-bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)disulfide (42977-21-9)

Conditions	Yield
With sodium hydroxide In methanol for 3h; Hydroformylation; Oxidative dimerization; Heating;	A 68% B n/a

2-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluoro-decyl)-isothiourea; hydriodide → 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3)

Conditions	Yield
With sodium hydroxide In water at 78 - 80℃; for 1h;	62%

2-(n-perfluorooctyl)ethyl iodide (2043-53-0) → 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3)

Conditions	Yield
With thiourea In ethanol for 72h; Heating;	52%
Multi-step reaction with 2 steps 1: NaOMe / methanol / 5 h / 70 °C 2: 68 percent / aq. NaOH / methanol / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: ethanol / 20 h / 79 °C 2: 62 percent / NaOH / H2O / 1 h / 78 - 80 °C View Scheme
Multi-step reaction with 2 steps 1: 5percent trioctylmethylammonium chloride / H2O / 16 h / 100 °C 2: basic hydrolysis View Scheme

2-(n-perfluorooctyl)ethyl iodide (2043-53-0) + thiourea (17356-08-0) → 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3)

Conditions	Yield
With sodium hydroxide 1.) EtOH, reflux; Multistep reaction;

(diaminomethylene)(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfonium iodide → 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3)

Conditions	Yield
basic hydrolysis; Yield given;

1-iodoheptadecafluorooctane (507-63-1) → 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / benzoyl peroxide / 2 h / 92 - 101 °C 2: ethanol / 20 h / 79 °C 3: 62 percent / NaOH / H2O / 1 h / 78 - 80 °C View Scheme

3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one (1318074-61-1) → 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: samarium diiodide / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere 1.2: 80 °C / Inert atmosphere; Sealed tube 2.1: tributylphosphine; water / tetrahydrofuran / 9 h / 20 °C / Inert atmosphere View Scheme

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + methyl vinyl ketone (78-94-4) → 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-butan-2-one

Conditions	Yield
With sodium methylate at 25℃; for 15h; Addition;	100%

N-(2-benzenesulfonylethyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-oxoacetamide + 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → 3-(2-benzenesulfonylethyl)-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-7,8-dimethoxy-1,3,4,5-tetrahydrobenzo[d]azepin-2-one

Conditions	Yield
Stage #1: N-(2-benzenesulfonylethyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-oxoacetamide; 1H,1H,2H,2H-Perfluorodecanethiol In dichloromethane for 18h; Pummerer reaction; Stage #2: With trifluoroacetic anhydride In dichloromethane for 1h; Stage #3: With boron trifluoride diethyl etherate In dichloromethane for 1h;	100%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → 2-chloro-4,6-bis(1H,1H,2H,2H-perfluorodecylthio)-1,3,5-triazine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃;	100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 1 - 2℃; for 2.5h; Inert atmosphere; Schlenk technique;	91%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → 2,4-dichloro-6-(1H,1H,2H,2H-perfluorodecylthio)-1,3,5-triazine (916667-82-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	100%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → 1,2-bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)disulfide (42977-21-9)

Conditions	Yield
With hydrogenchloride; iodine; dimethyl sulfoxide for 1.16667h; Oxidation; Heating;	99.7%
With dihydrogen peroxide In acetic acid at -28℃; for 18h; Oxidation;
Multi-step reaction with 2 steps 1: MCPBA / ethyl acetate / 12 h / -28 °C 2: 79.2 percent / aq. NaOH / ethanol / 15.3 h / 30 - 33 °C View Scheme

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + ethyl 3-nitro-9-oxo-9H-thioxanthene-1-carboxylate (81116-45-2) → ethyl 3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio)-9-oxo-9H-thioxanthene-1-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 1h;	99%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + 4-Carboxybenzaldehyde (619-66-9) → 4-Carboxy-benzaldehyde-bis-(1,1,2,2-tetrahydroperfluorodecylthio)-acetal

Conditions	Yield
With hydrogenchloride In toluene	99%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + 1-allyl-3-methylimidazol-3-ium N-bis(trifluoromethanesulfonyl)imidate (655249-87-9) → 1-methyl-3-[3-(1H,1H,2H,2H-perfluorodecylthio)propyl]imidazolium bis(trifluoromethanesulfonyl)imide

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In methanol; dichloromethane for 1h; UV-irradiation;	99%

4-bromoethylbutanoate (2969-81-5) + 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-butyric acid ethyl ester (220072-48-0)

Conditions	Yield
With sodium ethanolate In ethanol 1.) 1 h, 2.) 0 deg C, 2 h; r.t., 4 h;	98%

N-[2-(3,4-dimethoxyphenyl)ethyl]-2-oxo-N-pentylacetamide + 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → 1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-7,8-dimethoxy-3-pentyl-1,3,4,5-tetrahydrobenzo[d]azepin-2-one (847550-46-3)

Conditions	Yield
Stage #1: N-[2-(3,4-dimethoxyphenyl)ethyl]-2-oxo-N-pentylacetamide; 1H,1H,2H,2H-Perfluorodecanethiol In dichloromethane for 18h; Pummerer reaction; Stage #2: With trifluoroacetic anhydride In dichloromethane for 1h; Stage #3: With boron trifluoride diethyl etherate In dichloromethane for 1h;	98%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + 1,3-bis(allyl)imidazolium bis(trifluoromethanesulfonyl)imide → 1,3-bis[3-(1H,1H,2H,2H-perfluorodecylthio)propyl]imidazolium bis(trifluoromethanesulfonyl)imide

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In methanol; dichloromethane for 1h; UV-irradiation;	98%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + β,β,β-trichloroethoxysulfonyl isocyanate (22959-55-3) → 2-Perfluorooctylethyl-N-(2,2,2-trichloroethoxysulfonyl)thiocarbamate

Conditions	Yield
at 20℃; for 0.0166667h; Addition;	97%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + 2-propenamide (79-06-1) → 3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-propionamide

Conditions	Yield
With sodium methylate at 25℃; for 18h; Addition;	96.4%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + C7H4FNO4S → 2-Perfluorooctylethyl-N-(4-fluorophenoxysulfonyl)thiocarbamate

Conditions	Yield
at 20℃; for 0.0166667h; Addition;	96%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + N-(2-nitrobenzenesulfonyl)-L-serine methyl ester (198836-50-9) → (S)-serine methyl ester (2788-84-3) + 1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-2-nitro-benzene

Conditions	Yield
With potassium carbonate In acetonitrile at 50℃; for 16h;	A 96% B n/a

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + acrylic acid (79-10-7) → 3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-propanoic acid (54207-62-4)

Conditions	Yield
With tetrabutyl ammonium fluoride at 50℃; for 10h;	96%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + C7H9N2(1+)*C8H18NO4S2(1-) → 1-methyl-3-[2,3-bis(1H,1H,2H,2H-perfluorodecylthio)propyl]imidazolium bis(trifluoromethanesulfonyl)imide

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In methanol; dichloromethane for 1h; UV-irradiation;	96%

1,3,5-Trioxan (110-88-3) + 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → (F-octyl-2 ethylthio) methanol (114857-07-7)

Conditions	Yield
With triethylamine at 0℃; Mechanism;	95%
With triethylamine at 0℃;	95%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + <(4-nitrophenyl)oxy>sulfonyl isocyanate (73748-48-8) → 2-Perfluorooctylethyl-N-(4-nitrophenoxysulfonyl)thiocarbamate

Conditions	Yield
at 20℃; for 0.0166667h; Addition;	95%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + (E,E,E)-1,6,11-tris[(4-fluorophenyl)sulfonyl]-1,6,11-triazacyclopentadeca-3,8,13-triene (501682-78-6) → (E,E,E)-1,6,11-tris[4-(1H,1H,2H,2H-perfluorodecylthio)phenylsulfonyl]-1,6,11-triazacyclopentadeca-3,8,13-triene

Conditions	Yield
With tetrabutyl-ammonium chloride; caesium carbonate In tetrahydrofuran	95%
With tetrabutyl-ammonium chloride; caesium carbonate In tetrahydrofuran at 20℃; for 20h;

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + ethyl bromoacetate (105-36-2) → ethyl 2-(perfluorooctyl)ethylthioacetate (87851-88-5)

Conditions	Yield
With triethylamine In acetone at 20℃; for 0.166667h;	94%
With sodium ethanolate In ethanol 1.) 1 h, 2.) 0 deg C, 2 h; r.t., 4 h;	92%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + 3,3'-(1,10-decadiyl)bis-1,1'-allylimidazolium bromide → 3,3'-(1,10-decadiyl)bis-1,1'-[3-(1H,1H,2H,2H-perfluorodecylthio)propyl]imidazolium bromide

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In methanol; dichloromethane for 1h; UV-irradiation;	94%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + 1,3-bis(2-propenyl)imidazolium bromide → 1,3-bis[3-(1H,1H,2H,2H-perfluorodecylthio)propyl]imidazolium bromide

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In methanol; dichloromethane for 1h; UV-irradiation;	94%

α-allyl-ω-allyloxytetra(oxyethylene) (58185-54-9) + 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-(3-{2-[2-(2-{2-[3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-propoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propylsulfanyl)-decane

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70℃; for 10h;	93%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + 4-(methoxycarbonyloxy)benzoic acid (14180-11-1) → 4-methoxycarbonyloxy-thiobenzoic acid S-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl) ester (877455-68-0)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	93%
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + C20H36O14S2Si8 → C80H66F102O14S8Si8

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran; chloroform for 0.666667h; UV-irradiation;	93%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + 3,5-dibromobenzaldehyde (56990-02-4) → 3,5-bis((3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)thio)benzaldehyde

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0) In toluene for 12h; Schlenk technique; Inert atmosphere; Reflux;	93%

2,3,4,5,6-pentafluorobiphenyl (784-14-5) + 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → 2,3,5,6-tetrafluoro-4-[(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-yl)sulfanyl]biphenyl

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2h; Inert atmosphere; regioselective reaction;	92%

1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) + C20H36O14S2Si8 → C80H66F102O14S8Si8

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran; chloroform for 0.666667h; UV-irradiation;	92%

ethyl-2-bromooctanoate (138286-76-7, 5445-29-4) + 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → 2-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-octanoic acid ethyl ester (220072-56-0)

Conditions	Yield
With sodium ethanolate In ethanol 1.) 1 h, 2.) 0 deg C, 2 h; r.t., 4 h;	91%

Upstream product

• 2043-53-0 2-(n-perfluorooctyl)ethyl iodide 
• 17356-08-0 thiourea 
• 42977-21-9 1,2-bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)disulfide 
• 1318074-61-1 3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one 
• 507-63-1 1-iodoheptadecafluorooctane 
• 125640-21-3 S-[2-(perfluorooctyl)ethyl]thioacetate 

Downstream Products

• 42977-21-9 1,2-bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)disulfide 
• 54207-62-4 3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-propanoic acid 
• 36880-12-3 2-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-propan-1-ol 
• 36880-07-6 2-perfluorooctyl-ethyl 3-hydroxy-propyl sulfide 
• 100-46-9 benzylamine 
• 103-67-3 benzyl-methyl-amine 
• 288-32-4 1H-imidazole 
• 2788-84-3 (S)-serine methyl ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 123-82-0 2-heptylamine 
• 588-46-5 N-(phenylmethyl)acetamide 

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The invention describes a process for reducing the surface energy of organic materials such as for example increasing the oil and water repellency and stain release of organic materials, which comprises treating the organic material with at least a compound of the formula I wherein the general symbols are as defined in claim 1; especially wherein at least one of the radicals R2, R3 or R4 is —CH(R11)—S(O)p—R12; R11 is hydrogen, C1-C8alkyl, unsubstituted or with C1-C4alkyl substituted phenyl; R12 is a monovalent perfluorinated alkyl or alkenyl, linear or branched organic radical having four to twenty fully fluorinated carbon atoms, and p is 0, 1 or 2.

Free-radical addition of 2-(perfluoroalkyl)ethanethiols to alkenes, alkadienes, cycloalkenes, alkynes and vinyl monomers

The free-radical addition of 2-(perfluoroalkyl)ethanethiols (RFCH2CH2SH) to alkenes, cycloalkenes, alkadienes and alkynes has been studied to determine: (1) the mode of reaction, i.e. the stereochemistry, regiochemistry and any skeletal changes: (2) the relative reactivity towards unsaturates of differing structures and classes as affected by the presence of the RF group; and (3) the influence of the reaction conditions on the rate of addition or selectivity for different products.Adducts from 2-(F-hexyl)ethanethiol (1) and alkenes have been obtained in high yield,but containing small amounts of regio isomers.For example compound 1 with 1-heptene gave 1-heptane (3, 96percent yield) as well as 2-heptane (4, O.61percent) and 3-heptane (5, 2.22percent). 1,6-Hexadiene and 1,7-octadiene gave chiefly linear adducts, i.e.RFCH2CH2S(CH2)nCH=CH2 (7, n=4; or 12, n=6, respectively) and RFCH2CH2S(CH2)nSCH2CH2RF (8, n=6; or 14, n=8, respectively).A small amount (2-3percent) of cis- and trans-1-methyl-cyclohexane (13) isomers were present in 12.Compound 1 with 1,6-heptadiene gave 7--1-heptene (9), the bis adduct, 1,7-bis-heptane (11) and the cyclic adducts, cis- and trans-1-methal-2-methylcyclopentane (10).The relative amounts of cyclic isomers depended on the reactant ratio.Compound 1 added readily with free-radical initiation to vinyl monomers such as styrene and vinyl acetate, and to phenyl acetylene, propargyl acetate and ethyl propynoate.These new addition products are useful as models for further study.