765-03-7

Basic information

• Product Name: 1-DODECYNE
• Synonyms: 1-DODECYNE;TIMTEC-BB SBB008732;1-C12H22;dodec-1-yne;1-Dodecyne,97%;Dodecane-1-yne;1-Dodecyne,98%;1-DODECYNE 99%
• CAS NO: 765-03-7
• Molecular Formula: C₁₂H₂₂
• Molecular Weight: 166.3
• EINECS: 212-134-9
• Product Categories: Acetylenes;Acetylenic Hydrocarbons;Alkynes;Organic Building Blocks;Terminal
• Mol File: 765-03-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: −19 °C(lit.)
• Boiling Point: 215 °C(lit.)
• Flash Point: 175 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.778 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.222mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Water Solubility: Not miscible in water.
• BRN: 1741320
• CAS DataBase Reference: 1-DODECYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-DODECYNE(765-03-7)
• EPA Substance Registry System: 1-DODECYNE(765-03-7)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 765-03-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

1-Dodecyne was used in the synthesis of stable ruthenium nanoparticles.

InChI:InChI=1/C12H22/c1-3-5-7-9-11-12-10-8-6-4-2/h1H,4-12H2,2H3

Synthetic route

6-dodecyne (6975-99-1) → 1-dodecyne (765-03-7)

Conditions	Yield
With potassium salt of 1,3-diaminopropane In tetrahydrofuran at 0℃; for 0.5h; other reagent;	97%
With sodium amide; mineral oil at 210℃;

(Z)-1-dimethylphenylsilyl-2-iodo-1-dodecene (86014-21-3) → 1-dodecyne (765-03-7)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran; dimethyl sulfoxide at 80℃; for 0.25h;	95%

1-trimethylsilyldodec-1-yne (121134-52-9) → 1-dodecyne (765-03-7)

Conditions	Yield
With silver nitrate In water; acetone at 20 - 55℃; for 48h;	92%

5-dodecyne (19780-12-2) → 1-dodecyne (765-03-7)

Conditions	Yield
With lithium 2-aminoethylamide In ethylenediamine for 0.333333h; amide-hydrocarbon ratio 3.5:1;	85%

undecylaldehyde (112-44-7) + ROMPgel-supported ethyl 1-diazo-2-oxopropylphosphonate → 1-dodecyne (765-03-7)

Conditions	Yield
With potassium carbonate In methanol at 4℃; for 36h; Horner-Wadsworth-Emmons reaction;	70%

1-bromo dodecane (112-29-8) + 4-chloro-2-methylbut-3-yn-2-ol (29552-15-6) → 1-dodecyne (765-03-7)

Conditions	Yield
With magnesium In tetrahydrofuran; benzene at 50 - 65℃; for 4h;	52.3%

lithium 1-phenylethenolate (1052762-47-6) + 1-dodecenyl phenyl selenone (88841-79-6) → 1-dodecyne (765-03-7) + 2-decylcyclopropyl phenyl ketone (73985-89-4)

Conditions	Yield
	A 19% B 41%

1,2-Dibromododecane (55334-42-4) → 1-dodecyne (765-03-7)

Conditions	Yield
With potassium hydroxide
With potassium hydroxide; sodium hydride 1.) water, EtOH, reflux, 2 h, 2.) DMSO, 10 deg C, 1 h; Yield given. Multistep reaction;

1-bromo dodecane (112-29-8) + sodium acetylide (1066-26-8) → 1-dodecyne (765-03-7)

Conditions	Yield
With ammonia; sodium amide under 5884.06 Torr;
With ammonia; N,N-dimethyl-formamide nach Entfernung des Ammoniaks bei 65-70grad;

Iododecane (2050-77-3) + sodium acetylide (1066-26-8) → 1-dodecyne (765-03-7)

Conditions	Yield
With ammonia unter Druck;

2-decyne (629-49-2) → 1-dodecyne (765-03-7)

Conditions	Yield
With sodium at 180 - 220℃;

nonylmagnesium bromide (39691-62-8) + 2-bromoallyl bromide (513-31-5) → 1-dodecyne (765-03-7)

Conditions	Yield
(i) , (ii) NaNH2, liq. NH3; Multistep reaction;

methanol (67-56-1) + cyclododecene (1501-82-2) → 1-dodecene (112-41-4) + 1-dodecyne (765-03-7) + Cyclododecyl methyl ether (2986-54-1) + bicyclo<7.3.0>dodecane (51302-77-3, 134287-08-4)

Conditions	Yield
for 60h; Irradiation;	A 2 % Chromat. B 4 % Chromat. C 11 % Chromat. D 15 % Chromat.

cyclododecene (1501-82-2) → 1-dodecene (112-41-4) + 1-dodecyne (765-03-7) + cyclododecane (294-62-2) + Cyclododecyl methyl ether (2986-54-1) + bicyclo<7.3.0>dodecane (51302-77-3, 134287-08-4) + 1,2-epoxycyclododecane (286-99-7)

Conditions	Yield
Product distribution; Mechanism; Irradiation; yields in pentane or methanol or methanol-d1;

cyclododecene (1501-82-2) → 1-dodecene (112-41-4) + 1-dodecyne (765-03-7) + Cyclododecyl methyl ether (2986-54-1) + bicyclo<7.3.0>dodecane (51302-77-3, 134287-08-4)

Conditions	Yield
In methanol for 60h; Irradiation;	A 2 % Chromat. B 4 % Chromat. C 11 % Chromat. D 15 % Chromat.

1-bromo dodecane (112-29-8) + lithium acetylide (70277-75-7) → 1-dodecyne (765-03-7)

Conditions	Yield
In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78 - 90℃; for 2h;

trans-1,2-dichloroethylene (156-60-5) + 1-Decene (872-05-9) → 1-dodecyne (765-03-7)

Conditions	Yield
With hydrogenchloride; Schwartz's reagent; 2,2,6,6-tetramethylpiperidinyl-lithium Yield given; Multistep reaction;

6-dodecyne (6975-99-1) + sodium amide + mineral oil → 1-dodecyne (765-03-7)

Conditions	Yield
at 210℃;

2-decyne (629-49-2) + sodium → 1-dodecyne (765-03-7)

Conditions	Yield
at 220℃;

1-bromo dodecane (112-29-8) + acetylene (74-86-2) → 1-dodecyne (765-03-7)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 20 - 68℃;
With sodium hydride In dimethyl sulfoxide; mineral oil at 20 - 68℃; Reagent/catalyst; Solvent;

1-dodecyne (765-03-7) → 1-dodecene (112-41-4)

Conditions	Yield
Stage #1: 1-dodecyne With indium(III) chloride; triethyl borane; diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 2.5h; Stage #2: With hydrogen cation In tetrahydrofuran Further stages.;	100%
Stage #1: 1-dodecyne With triethyl borane; dichloroindium hydride In tetrahydrofuran; hexane at -78℃; for 2.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane	98%
With pyridine; Dimethylphenylsilane; water In acetonitrile at 80℃; for 8h;	98%

1-dodecyne (765-03-7) + zinc-2,4-diiododeuteroporphyrin-IX dimethyl ester → zinc-2,4-bis(dodecynyl)deuteroporphyrin-IX dimethyl ester

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine; N,N-dimethyl-formamide at 20℃; for 36h; Heck reaction;	100%

2-bromo-6-(3-hydroxy-3-methyl-1-butynyl)-4-octyloxypyridine (1032413-36-7) + 1-dodecyne (765-03-7) → 2-(1-dodecynyl)-6-(3-hydroxy-3-methyl-1-butynyl)-4-octoxypyridine (1032413-72-1)

Conditions	Yield
With copper(l) iodide; diethylamine; bis-triphenylphosphine-palladium(II) chloride at 20℃; for 2.5h; Sonogashira reaction;	100%

lithium tris(triphenylgermyl)manganate(II) + 1-dodecyne (765-03-7) → (E)-1-triphenylgermyl-1-dodecene (92740-99-3)

Conditions	Yield
With butan-1-ol In tetrahydrofuran 1-dodecyne (0.5 mmol) treated with germylmanganate (0.6 mmol) in THF inthe presence of n-BuOH (2.0 mmol) at 25°C for 4.5 h;	100%

1-dodecyne (765-03-7) + 2'-azido-2'-deoxyuridine (26929-65-7) → C21H33N5O5 (1223357-62-7)

Conditions	Yield
With copper(II) sulphate hydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 48h; Huisgen cycloaddition;	100%

1-dodecyne (765-03-7) + paracetaldehyde (123-63-7) → tridec-2-yn-1-ol (51887-25-3)

Conditions	Yield
Stage #1: 1-dodecyne With n-butyllithium In tetrahydrofuran at 5℃; for 0.5h; Inert atmosphere; Stage #2: paracetaldehyde In tetrahydrofuran at 5 - 20℃;	100%

1-bromo-1-fluoroethylene (420-25-7) + 1-dodecyne (765-03-7) → C14H23F (1432736-79-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere; Cooling with acetone-dry ice;	100%

m-iodonitrobenzene (645-00-1) + 1-dodecyne (765-03-7) → 1-(dodec-1-yn-1-yl)-3-nitrobenzene (187871-27-8)

Conditions	Yield
With copper(l) iodide; diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran Ambient temperature;	99%
With triethylamine In water for 2h; Sonogashira Cross-Coupling; Heating;	78%

1-dodecyne (765-03-7) → tetracosa-11,13-diyne (24574-07-0)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide; ethyl bromoacetate; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃;	99%
With 1,10-Phenanthroline; dicobalt octacarbonyl; carbon monoxide In acetonitrile at 80℃; under 760 Torr; for 18h;	91%
With N,N,N,N,-tetramethylethylenediamine; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; copper(l) chloride at 20℃; for 7h; Glaser oxidative coupling;	90%

1-dodecyne (765-03-7) + copper-2,4-diiododeuteroporphyrin-IX dioctyl ester → copper-2,4-bis-(1'-dodecynyl)deuteroporphyrin-IX dioctyl ester

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 20℃; for 24h; Heck reaction;	99%

1-dodecyne (765-03-7) → dodecane (112-40-3)

Conditions	Yield
With C30H37ClN4ORu; hydrogen; sodium t-butanolate In toluene at 105℃; under 4500.45 Torr; for 20h; Glovebox; Sealed tube;	99%
With diethyl ether for 24h; Milling;	86%
With palladium 10% on activated carbon; hydrogen at 20℃; for 24h; Neat (no solvent);	83%

1-dodecyne (765-03-7) → 1-deuterio-1-dodecyne (86014-19-9)

Conditions	Yield
Stage #1: 1-dodecyne With potassium carbonate In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Stage #2: With water-d2 In acetonitrile at 20℃; for 1h; Inert atmosphere;	99%
With n-butyllithium; water-d2 In diethyl ether; hexane	69%
With water-d2 at 50℃; for 8h;	65%
With water-d2 at 70℃;
With water-d2; potassium carbonate In acetonitrile at 50℃; for 24.5h; Inert atmosphere;

1-dodecyne (765-03-7) + triphenylgermane (2816-43-5) → (E)-1-triphenylgermyl-1-dodecene (92740-99-3)

Conditions	Yield
triethyl borane In hexane; benzene addn. of Et3B in hexane to a soln. of acetylene-compd. and a slight excess of Ph3GeH in benzene, heating at 60°C for 2 h; evapn., purifn. by column chromy. or preparative thin-layer chromy. on silica gel,; elem. anal.; isomer ratio Z/E=<1/20 (detd. by GC, NMR);	99%

1-dodecyne (765-03-7) + C23H32BrNO (1010685-26-3) → C35H53NO (1010685-27-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 100℃; for 36h; Sonogashira coupling; Inert atmosphere;	99%

1-dodecyne (765-03-7) + 2-bromo-4-nitrotoluene (7745-93-9) → 2-(dodec-1-yn-1-yl)-1-methyl-4-nitrobenzene (1052216-02-0)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); triethylamine; XPhos In water at 20℃; Sonogashira coupling; Inert atmosphere; Micellar solution;	99%
With dichloro bis(acetonitrile) palladium(II); SPGS-550-M; NOK; triethylamine; XPhos In water for 24h; Reagent/catalyst; Sonogashira Cross-Coupling; Inert atmosphere; Sealed tube;	98%

1-dodecyne (765-03-7) + 4β-azido-4-deoxy-4′-demethylepipodophyllotoxin (117604-05-4) → 4'-O-demethyl-4β-[(4-decyl)-1,2,3-triazol-1-yl]-4-desoxypodophyllotoxin (1310548-44-7)

Conditions	Yield
With copper(ll) sulfate pentahydrate; L-ascorbic acid sodium salt In water; tert-butyl alcohol at 20℃; for 8h;	99%

1-dodecyne (765-03-7) + 1-(2,6-dibromo-phenyl)-1H-pyrrole (1372804-17-5) → 1-(2,6-di(dodec-1-yn-1-yl)phenyl)-1H-pyrrole (1423468-70-5)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; tri-tert-butyl phosphine; diisopropylamine In 1,4-dioxane; toluene at 20℃; Inert atmosphere;	99%

1-dodecyne (765-03-7) + 1,1'-sulfinylbisbenzene (945-51-7) → racemic methyl phenyl sulfoxide (1193-82-4) + 1-(dodec-1-yn-1-yl)benzene (108604-35-9)

Conditions	Yield
Stage #1: 1-dodecyne; 1,1'-sulfinylbisbenzene With dichloro-[1,3-bis(2,6-diisopropylpenyl)-2-imidazolidinyliden]-(3-chloropyridyl)palladium(II); lithium tert-butoxide In tetrahydrofuran at 70℃; for 6h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere; Stage #2: With methyl iodide In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	A 98% B 99%

1-dodecyne (765-03-7) → 1-iodo-dodeca-1-yne (60705-20-6)

Conditions	Yield
With N-iodo-succinimide; silver nitrate In acetone at 20℃; for 1h; Darkness;	98%
With N-iodo-succinimide; silver nitrate In acetone at 20℃; for 1h; Darkness;	98%
With N-iodo-succinimide; acetic acid In acetonitrile at 80℃; for 1.5h; Molecular sieve;	93%

1-dodecyne (765-03-7) + zinc-2,4-diiododeuteroporphyrin-IX dioctyl ester → zinc-2,4-bis(1'-dodecynyl)deuteroporphyrin-IX dioctyl ester

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 20℃; for 24h; Heck reaction;	98%

1-dodecyne (765-03-7) + 1,4-bromoiodobenzene (589-87-7) → 4-(dodec-1-yne)bromobenzene

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 20℃; for 3.5h; Substitution;	98%

1-dodecyne (765-03-7) + methyl chloroformate (79-22-1) → methyl 2-tridecynoate (89199-80-4)

Conditions	Yield
Stage #1: 1-dodecyne With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: methyl chloroformate In tetrahydrofuran at 20℃;	98%

3-bromoquinoline (5332-24-1) + 1-dodecyne (765-03-7) → 3-(dodec-1-ynyl)quinoline (1052216-22-4)

Conditions	Yield
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; palladium diacetate; triethylamine In water at 20℃; Sonogashira coupling; Inert atmosphere; Micellar solution;	98%

1-dodecyne (765-03-7) + (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran (607715-89-9) → C47H56O5 (1234178-28-9)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine at 20℃; for 1h; Sonogashira coupling; Inert atmosphere;	98%

1-dodecyne (765-03-7) + 3,5-heptanedione (7424-54-6) → 4-(dodec-1-en-3-yl)heptane-3,5-dione

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 4-trifluoromethylbenzoic acid; bis[2-(diphenylphosphino)phenyl] ether In ethanol; 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere; Sealed tube; regioselective reaction;	98%

1-dodecyne (765-03-7) + tert-butyl (2R,4S)-4-((4-bromobenzyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidine-1-carboxylate → tert-butyl (2R,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-((E)-dodec-1-en-1-yl)benzyl)oxy)pyrrolidine-1-carboxylate

Conditions	Yield
Stage #1: 1-dodecyne With benzo[1,3,2]dioxaborole In tetrahydrofuran at 70℃; for 2h; Stage #2: tert-butyl (2R,4S)-4-((4-bromobenzyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidine-1-carboxylate With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In tetrahydrofuran; 1,2-dimethoxyethane; water at 85℃; for 5h; Suzuki-Miyaura Coupling;	98%

1-dodecyne (765-03-7) + tert-butyl (2S,4R)-4-((4-bromobenzyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidine-1-carboxylate → tert-butyl (2S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-((E)-dodec-1-en-1-yl)benzyl)oxy)pyrrolidine-1-carboxylate

Conditions	Yield
Stage #1: 1-dodecyne With benzo[1,3,2]dioxaborole In tetrahydrofuran at 70℃; for 2h; Stage #2: tert-butyl (2S,4R)-4-((4-bromobenzyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidine-1-carboxylate With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In tetrahydrofuran; 1,2-dimethoxyethane; water at 85℃; for 5h; Suzuki-Miyaura Coupling;	98%

1-dodecyne (765-03-7) + (Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid (1617539-93-1) → (Z)-2,3-O,O-dibenzyl-6-[4-decyl-1,2,3-triazole-1-yl]-4,5-didehydro-5,6-dideoxy-L-ascorbic acid

Conditions	Yield
With copper diacetate In methanol at 50℃; Temperature; Flow reactor; Sonication;	98%
With copper diacetate In methanol

1-dodecyne (765-03-7) + 1-iodo-2-((2-methylallyl)oxy)benzene (156642-47-6) → 3-methyl-3-tridec-2-ynyl-2,3-dihydro-1-benzofuran

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 0.25h; Microwave irradiation; Inert atmosphere; Sealed tube; Green chemistry;	98%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique;	98%

1-dodecyne (765-03-7) + 2-iodo-4-methyl-1-[(2-methylprop-2-enyl)oxy]benzene → 3,5-dimethyl-3-tridec-2-ynyl-2,3-dihydro-1-benzofuran

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 0.25h; Microwave irradiation; Inert atmosphere; Sealed tube; Green chemistry;	98%

Upstream product

• 112-29-8 1-bromo dodecane 
• 1066-26-8 sodium acetylide 
• 2050-77-3 Iododecane 
• 67-56-1 methanol 
• 1501-82-2 cyclododecene 
• 70277-75-7 lithium acetylide 
• 112-44-7 undecylaldehyde 
• 74-86-2 acetylene 
• 121134-52-9 1-trimethylsilyldodec-1-yne 
• 29552-15-6 4-chloro-2-methylbut-3-yn-2-ol 
• 629-49-2 2-decyne 
• 6975-99-1 6-dodecyne 
• 156-60-5 trans-1,2-dichloroethylene 
• 872-05-9 1-Decene 

Downstream Products

• 94088-24-1 1,1-diethoxy-tridec-2-yne 
• 6714-01-8 2,4-dipropylbut-1-en-3-yne 
• 88472-58-6 6-Methylene-hexadec-4-yne 
• 88472-55-3 13-methylene-11-tricosyne 
• 104066-66-2 (Z)-3-(Dimethyl-phenyl-silanyl)-1-phenyl-tridec-2-en-1-ol 
• 138924-72-8 (1Z,3E)-2-decyl-1,4-diphenyl-1,3-butadiene 
• 138924-71-7 (1E,3E)-2-decyl-1,4-diphenyl-1,3-butadiene 
• 77-73-6 bi(cyclopentadiene) 
• 55191-38-3 1,3-didecylbenzene 
• 104066-52-6 (E)-1-(triphenylsilyl)-1-dodecene 
• 104066-52-6 (Z)-1-(triphenylsilyl)-1-dodecene 
• 108025-31-6 (Z)-1-(dimethylphenylsilyl)-1-dodecene 
• 86014-02-0 (E)-1-(dimethylphenylsilyl)-1-dodecene 
• 6175-49-1 dodecan-2-one 

Relevant articles and documents

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