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690-94-8

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690-94-8 Usage

General Description

Dimethyl(vinyl)ethynylcarbinol is a chemical compound with the formula C6H10O. It is a colorless liquid with a distinct odor, and is used as a reagent in organic synthesis. Dimethyl(vinyl)ethynylcarbinol is commonly employed as an intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. It is known for its ability to act as a nucleophile in various reactions, and is often utilized in the creation of complex organic molecules. Overall, dimethyl(vinyl)ethynylcarbinol is a versatile and important chemical in the field of organic chemistry.

Check Digit Verification of cas no

The CAS Registry Mumber 690-94-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,9 and 0 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 690-94:
(5*6)+(4*9)+(3*0)+(2*9)+(1*4)=88
88 % 10 = 8
So 690-94-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H10O/c1-4-5-6-7(2,3)8/h4,8H,1H2,2-3H3

690-94-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-methylhex-5-en-3-yn-2-ol

1.2 Other means of identification

Product number -
Other names Nazarov carbinol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:690-94-8 SDS

690-94-8Synthetic route

Vinyl bromide
593-60-2

Vinyl bromide

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethylamine at 0 - 20℃; for 12h;91%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium hydroxide In tetrahydrofuran; diethylamine at 0 - 20℃; for 12h;91%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 23℃; for 2.5h;84%
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethylamine at 23℃; for 2.5h;84%
With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; Sonogashira coupling;80%
(vinyl)trimethoxylsilane
2768-02-7

(vinyl)trimethoxylsilane

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; copper diacetate In 1,4-dioxane at 30℃;47%
Vinyl bromide
593-60-2

Vinyl bromide

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

A

2,7-dimethyl-octa-3,5-diyne-2,7-diol
5929-72-6

2,7-dimethyl-octa-3,5-diyne-2,7-diol

B

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 20℃; Inert atmosphere;A 20%
B 42%
3-buten-1-yne
689-97-4

3-buten-1-yne

acetone
67-64-1

acetone

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

Conditions
ConditionsYield
With diethyl ether unter starkem Kuehlen mit KOH;
With potassium hydroxide; sodium hydroxide
With diethyl ether unter starkem Kuehlen mit NaNH2;
With potassium hydroxide In ammonia at 30 - 40℃;
1,4-dichloro-2-butene
764-41-0

1,4-dichloro-2-butene

acetone
67-64-1

acetone

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

Conditions
ConditionsYield
With ammonia; sodium amide
3,4-dichlorobut-1-ene
310447-99-5, 310448-01-2

3,4-dichlorobut-1-ene

acetone
67-64-1

acetone

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

Conditions
ConditionsYield
With ammonia; sodium amide
3-buten-1-ynylmagnesium bromide
14763-72-5

3-buten-1-ynylmagnesium bromide

acetone
67-64-1

acetone

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

Conditions
ConditionsYield
With diethyl ether
With diethyl ether
With diethyl ether
3-buten-1-yne
689-97-4

3-buten-1-yne

2-hydroxy-2-methylpropiophenone
7473-98-5

2-hydroxy-2-methylpropiophenone

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

Conditions
ConditionsYield
With ammonia; sodium; ferric nitrate
5-chloro-5-methyl-1-hexen-3-yne
819-44-3

5-chloro-5-methyl-1-hexen-3-yne

water
7732-18-5

water

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

5-bromo-5-methyl-hex-1-en-3-yne
20728-33-0

5-bromo-5-methyl-hex-1-en-3-yne

KOH

KOH

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

5-chloro-5-methyl-1-hexen-3-yne
819-44-3

5-chloro-5-methyl-1-hexen-3-yne

diethyl ether
60-29-7

diethyl ether

silver carbonate

silver carbonate

A

1,1,3,3-Tetramethyl-4-vinyl-phthalan
16806-78-3

1,1,3,3-Tetramethyl-4-vinyl-phthalan

B

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

C

2-methyl-hexa-1,5-dien-3-yne
820-54-2

2-methyl-hexa-1,5-dien-3-yne

Conditions
ConditionsYield
at 0℃;
tetrabutoxytitanium

tetrabutoxytitanium

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

(C4H9O)3Ti(OC(CH3)2CCCHCH2)
96301-49-4

(C4H9O)3Ti(OC(CH3)2CCCHCH2)

Conditions
ConditionsYield
In benzene byproducts: BuOH; react. of Ti(OBu)4 with the alcohol under azeotropic distn. of BuOH (20-60°C, 1-3 h, inert atmosphere); evapn. (< 0.2 mm), vac. distn.; elem. anal.;95%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

1-chloro-5-methylhex-3-yne-2,5-diol
1021867-45-7

1-chloro-5-methylhex-3-yne-2,5-diol

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide at 54.84℃; for 7.5h; Product distribution; Kinetics; Further Variations:; Temperatures; reagent concentrations, reaction time;94.3%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

1-bromo-5-methylhex-3-yne-2,5-diol
125510-58-9

1-bromo-5-methylhex-3-yne-2,5-diol

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide at 54.84℃; for 7.5h; Product distribution; Further Variations:; Temperatures; reagent concentrations, reaction time;92.8%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

methyl iodide
74-88-4

methyl iodide

5-methoxy-5-methylhex-1-en-3-yne
814-57-3

5-methoxy-5-methylhex-1-en-3-yne

Conditions
ConditionsYield
Stage #1: dimethyl(vinylethynyl)carbinol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃;
90%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

4-methoxybenzoic acid 1,1-dimethylpent-4-en-2-ynyl ester
866487-22-1

4-methoxybenzoic acid 1,1-dimethylpent-4-en-2-ynyl ester

Conditions
ConditionsYield
With pyridine at 90℃; for 14h;89%
In pyridine at 90℃; for 14h;89%
C5Cl4H2C2H3COCl

C5Cl4H2C2H3COCl

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

C15H14Cl4O2

C15H14Cl4O2

Conditions
ConditionsYield
With triethylamine In benzene at 80℃; for 5h;88%
C5Cl4H2C2H3COClO2C2H4

C5Cl4H2C2H3COClO2C2H4

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

C17H18Cl4O4

C17H18Cl4O4

Conditions
ConditionsYield
With triethylamine In benzene at 80℃; for 5h;88%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

2-methyl-hexa-1,5-dien-3-yne
820-54-2

2-methyl-hexa-1,5-dien-3-yne

Conditions
ConditionsYield
With ion-exchange resin KU-23 at 30℃; under 100 Torr; for 2h; Dehydration;87%
With sulfuric acid at 10 - 65℃; for 4.5h;73%
With sulfuric acid at 70℃;
With sulfuric acid
With benzenesulfonyl chloride In pyridine
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

(1R,2R,4S)-1,4,5,6,7,7-Hexachloro-bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

(1R,2R,4S)-1,4,5,6,7,7-Hexachloro-bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

C15H12Cl6O2

C15H12Cl6O2

Conditions
ConditionsYield
With triethylamine In benzene at 80℃; for 5h;87%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyldimethyl((2-methylhex-5-en-3-yn-2-yl)oxy)silane
1048027-89-9

tert-butyldimethyl((2-methylhex-5-en-3-yn-2-yl)oxy)silane

Conditions
ConditionsYield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 65℃; for 16h; Inert atmosphere;86%
o-tetrachloroquinone
2435-53-2

o-tetrachloroquinone

dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

1,4,5,6-Tetrachloro-7-(3-hydroxy-3-methyl-but-1-ynyl)-bicyclo[2.2.2]oct-5-ene-2,3-dione
66481-31-0

1,4,5,6-Tetrachloro-7-(3-hydroxy-3-methyl-but-1-ynyl)-bicyclo[2.2.2]oct-5-ene-2,3-dione

Conditions
ConditionsYield
With hydroquinone In toluene at 108℃; for 18h;85.3%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

1-cyclohexyl-2,5-dimethylhex-3-yne-1,5-diol

1-cyclohexyl-2,5-dimethylhex-3-yne-1,5-diol

Conditions
ConditionsYield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); isopropyl alcohol; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 90℃; for 48h; Inert atmosphere; Sealed tube; diastereoselective reaction;85%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

(E)-2-methyl-3,5-hexadien-2-ol
69514-47-2

(E)-2-methyl-3,5-hexadien-2-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride82%
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride; water 1.) ether, 20 deg C; Multistep reaction;
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

5,6-dibromo-2-methylhex-3-yn-2-ol
98333-78-9

5,6-dibromo-2-methylhex-3-yn-2-ol

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide at 39.84℃; for 4h;82%
With chloroform; bromine
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

p-toluenesulfonyl iodide
1950-78-3

p-toluenesulfonyl iodide

A

Toluene-4-sulfonic acid 1,1-dimethyl-pent-4-en-2-ynyl ester

Toluene-4-sulfonic acid 1,1-dimethyl-pent-4-en-2-ynyl ester

B

5-Iodo-2-methyl-6-(toluene-4-sulfonyl)-hex-3-yn-2-ol
88966-64-7

5-Iodo-2-methyl-6-(toluene-4-sulfonyl)-hex-3-yn-2-ol

Conditions
ConditionsYield
In acetonitrile at 110℃; for 96h; Yields of byproduct given. Title compound not separated from byproducts;A n/a
B 80%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

5,6-dichloro-2-methylhex-3-yn-2-ol
1021867-52-6

5,6-dichloro-2-methylhex-3-yn-2-ol

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide at 39.84℃; for 4h;78%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

isobutyraldehyde
78-84-2

isobutyraldehyde

2,5,7-trimethyloct-3-yne-2,6-diol

2,5,7-trimethyloct-3-yne-2,6-diol

Conditions
ConditionsYield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); isopropyl alcohol; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 100℃; for 48h; Reagent/catalyst; Time; Inert atmosphere; Sealed tube; diastereoselective reaction;73%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

C14H22(2)H2O2

C14H22(2)H2O2

Conditions
ConditionsYield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); d8-isopropanol; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 90℃; for 48h; Inert atmosphere; Sealed tube;72%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

chloroform
67-66-3

chloroform

4-(2,2-Dichloro-cyclopropyl)-2-methyl-but-3-yn-2-ol

4-(2,2-Dichloro-cyclopropyl)-2-methyl-but-3-yn-2-ol

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water at 28 - 30℃; for 4h;69%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

2-hydroxy-5,5-dimethyl-4-vinyl-1,2-oxaphosphol-3-ene 2-oxide

2-hydroxy-5,5-dimethyl-4-vinyl-1,2-oxaphosphol-3-ene 2-oxide

Conditions
ConditionsYield
With hydrogenchloride; air; hypophosphorous acid68%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

diphenyl 3-methylhexa-1,3,4-trien-3-yl phosphine oxide
1384384-68-2

diphenyl 3-methylhexa-1,3,4-trien-3-yl phosphine oxide

Conditions
ConditionsYield
With triethylamine In dichloromethane at -70 - 20℃; for 5h;65%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

(5-methyl-1,3,4-hexatrien-3-yl)phosphonous acid
89206-87-1

(5-methyl-1,3,4-hexatrien-3-yl)phosphonous acid

Conditions
ConditionsYield
With hypophosphorous acid62%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

triisopropyl((2-methylhex-5-en-3-yn-2-yl)oxy)silane
1379656-67-3

triisopropyl((2-methylhex-5-en-3-yn-2-yl)oxy)silane

Conditions
ConditionsYield
Stage #1: dimethyl(vinylethynyl)carbinol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: triisopropylsilyl chloride In tetrahydrofuran at 0 - 20℃;
60%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

2,2,3,3-tetrafluoropropanol
76-37-9

2,2,3,3-tetrafluoropropanol

dimethylvinylethynylcarbinol 1,1,3-trihydroperfluoropropyl ether

dimethylvinylethynylcarbinol 1,1,3-trihydroperfluoropropyl ether

Conditions
ConditionsYield
With sulfuric acid; hydroquinone at 20℃; for 20h;58%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

methylsulphinyl chloride
676-85-7

methylsulphinyl chloride

5-methyl-3-(methylsulfonyl)hexa-1,3,4-triene
753007-62-4

5-methyl-3-(methylsulfonyl)hexa-1,3,4-triene

Conditions
ConditionsYield
Stage #1: dimethyl(vinylethynyl)carbinol; methylsulphinyl chloride With triethylamine In diethyl ether at -40 - 20℃;
Stage #2: In toluene for 5h; Heating;
55%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

pivalaldehyde
630-19-3

pivalaldehyde

2,5,7,7-tetramethyloct-3-yne-2,6-diol

2,5,7,7-tetramethyloct-3-yne-2,6-diol

Conditions
ConditionsYield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); isopropyl alcohol; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 90℃; for 48h; Inert atmosphere; Sealed tube; diastereoselective reaction;54%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

2,2-dimethyltetrahydropyran-4-one
1194-16-7

2,2-dimethyltetrahydropyran-4-one

Conditions
ConditionsYield
With sulfuric acid; water; mercury(II) sulfate at 85℃; for 5h;53%
With sulfuric acid; mercury(II) sulfate
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

2,2,3,3,4,4,5,5-octafluoropentan-1-ol
355-80-6

2,2,3,3,4,4,5,5-octafluoropentan-1-ol

dimethylvinylethynylcarbinol 1,1,5-trihydroperfluoropentyl ether

dimethylvinylethynylcarbinol 1,1,5-trihydroperfluoropentyl ether

Conditions
ConditionsYield
With sulfuric acid; hydroquinone at 20℃; for 20h;53%
dimethyl(vinylethynyl)carbinol
690-94-8

dimethyl(vinylethynyl)carbinol

2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine
613244-84-1, 71657-06-2

2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine

3,4-dimethyl-2-(3-methyl-1-vinyl-1,2-butadienyl)-5-phenyl-1,3,2-oxazaphospholidine 2-oxide

3,4-dimethyl-2-(3-methyl-1-vinyl-1,2-butadienyl)-5-phenyl-1,3,2-oxazaphospholidine 2-oxide

Conditions
ConditionsYield
With triethylamine In benzene for 5h;50.6%

690-94-8Relevant articles and documents

SUBSTITUTED IMIDAZOLECARBOXYLATE DERIVATIVES AND THE USE THEREOF

-

Paragraph 0912-0914; 1003-1004, (2020/12/08)

A compound is shown in formula (I). The derivatives of the compound include a stereoisomer, a pharmaceutically acceptable salt, a solvate, a prodrug, a metabolite, a deuterated derivative. The compound is a structurally novel substituted imidazole formate derivative. Substituted imidazole formate derivatives are used in preparing a drug with sedative, hypnotic and/or anesthetic effects, as well as a drug that can control the state of epilepsy. The compound has a good inhibitory effect on the central nervous system, and provides a new option for clinical screening of and/or preparation of a drug with sedative, hypnotic and/or anesthetic effects and controlling the state of epilepsy.

Ruthenium-catalyzed reductive coupling of 1,3-enynes and aldehydes by transfer hydrogenation: Anti-diastereoselective carbonyl propargylation

Geary, Laina M.,Leung, Joyce C.,Krische, Michael J.

supporting information, p. 16823 - 16827 (2013/03/28)

Under the conditions of ruthenium-catalyzed transfer hydrogenation employing isopropanol as a source of hydrogen, isopropoxy-substituted enyne 1 b and aldehydes 3 a-3 l engage in reductive coupling to provide products of propargylation 4 a-4 l with good to complete levels of anti- diastereoselectivity. The unprotected tertiary hydroxy moiety of isopropoxy enyne 1 b is required to enforce diastereoselectivity. Deuterium-labeling studies corroborate reversible enyne hydrometalation in advance of carbonyl addition. As demonstrated in the conversion of 4 f-h and 4 k to 5 f-h and 5 k, the isopropoxy group of the product is readily cleaved upon exposure to aqueous sodium hydroxide to reveal the terminal alkyne. Unprotected coupling is better! Ruthenium-catalyzed transfer hydrogenation of enynes in the presence of aldehydes promotes reductive C-C coupling to provide products of propargylation with good to complete levels of anti-diastereoselectivity (see scheme). The unprotected hydroxy group of the isopropoxy-substituted enyne is required to enforce high levels of anti-diastereoselectivity. Copyright

Regiocontrol of the palladium-catalyzed tin hydride addition to Z-enynols: Remarkable Z-directing effects

Hamze, Abdallah,Provot, Olivier,Brion, Jean-Daniel,Alami, Mouad

, p. 3868 - 3874 (2008/02/02)

(Figure Presented) Palladium-catalyzed hydrostannation of substituted Z- and E-enynols is discussed and compared. The regioselectivity of the H-Sn bond addition was found to be controlled by the geometry of the double bond (Z- or syn-directing effect) rather than the nature of its substituents, Exclusively α-vinyl stannanes were obtained from Z-enynols having various substituents on the double bond regardless of their electronic, steric, or chelating natures.

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