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p-Toluenesulfonamide is an organic compound with the chemical formula C7H7SO2NH2. It is a white crystalline solid that is soluble in water and has a slight amine-like odor. It is commonly used as an intermediate in the synthesis of various chemicals and pharmaceuticals.

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  • 70-55-3 Structure
  • Basic information

    1. Product Name: 4-Methylbenzenesulfonamide
    2. Synonyms: Tosylamide;Uniplex 173;4-TOLUENESULFONIC ACID AMIDE;4-TOLUENESULFONAMIDE;4-METHYLBENZENESULFONAMIDE;P-TOLUENESULFONAMIDE;P-TOLUENESULFONYLAMIDE;P-TOLUENESULPHONAMIDE
    3. CAS NO:70-55-3
    4. Molecular Formula: C7H9NO2S
    5. Molecular Weight: 171.22
    6. EINECS: 200-741-1
    7. Product Categories: SULFONAMIDE;FINE Chemical & INTERMEDIATES;Organic Building Blocks;Sulfonamides/Sulfinamides;Sulfur Compounds;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;T;pharmaceutical intermediate;Isoquinolines ,Quinolines ,Quinaldines
    8. Mol File: 70-55-3.mol
  • Chemical Properties

    1. Melting Point: 134-137 °C(lit.)
    2. Boiling Point: 221 °C (10 mmHg)
    3. Flash Point: 202 °C
    4. Appearance: White/Crystalline Powder
    5. Density: 1.2495 (rough estimate)
    6. Vapor Density: 5.9 (vs air)
    7. Vapor Pressure: 0.000285mmHg at 25°C
    8. Refractive Index: 1.6100 (estimate)
    9. Storage Temp.: Store below +30°C.
    10. Solubility: DMSO: soluble
    11. PKA: 10.20±0.10(Predicted)
    12. Water Solubility: 0.32 g/100 mL (25 º C)
    13. BRN: 472689
    14. CAS DataBase Reference: 4-Methylbenzenesulfonamide(CAS DataBase Reference)
    15. NIST Chemistry Reference: 4-Methylbenzenesulfonamide(70-55-3)
    16. EPA Substance Registry System: 4-Methylbenzenesulfonamide(70-55-3)
  • Safety Data

    1. Hazard Codes: Xi,Xn
    2. Statements: 36-20/21/22
    3. Safety Statements: 26-36
    4. WGK Germany: 1
    5. RTECS: XT5075000
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: III
    9. Hazardous Substances Data: 70-55-3(Hazardous Substances Data)

70-55-3 Usage

Uses

Used in Chemical Industry:
p-Toluenesulfonamide is used as an intermediate in the manufacture of dyes, synthetic resins, paints, disinfectants, and wood processing brighteners. It is also used for the production of plasticizers, disinfectants, and fluorescent dyes.
Used in Nickel Plating:
p-Toluenesulfonamide is used as a primary brightener in bright nickel plating for multilayer applications to obtain a uniform bright coating. The commonly used amount is 0.2~0.3 g/L.
Used in Organic Synthesis:
p-Toluenesulfonamide is used as a reagent in the synthesis of various organic compounds, resins, and saccharin.
Used in Pharmaceutical Industry:
p-Toluenesulfonamide is used to prepare the precursor required for the synthesis of ethyl 6-phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate, which is used in the development of antiglaucoma and anticancer drugs.
Used in Plasticizer, Disinfectant, and Fungicide Production:
p-Toluenesulfonamide is used in the manufacture of plasticizers, disinfectants, fungicides, and wood brighteners. It is also used in the production of synthetic resins, coatings, fluorescent dyes, and pharmaceuticals.

Role and purpose

P-toluene sulfonamide is a kind of excellent solid plasticizer used for thermoset plastic. It is suitable for being applied to phenolic resin, melamine resin, urea-formaldehyde resins and polyamide resins. Combination with a small amount can improve workability and make the solidification be uniform, and thus endowing the products with a good gloss. However, P-toluene sulfonamide has no softening effect as the liquid plasticizer, and is incompatible with polyvinyl chloride and vinyl chloride copolymer and is partially compatible with cellulose acetate, cellulose acetate butyrate and cellulose nitrate. p-Toluene sulfonamide has a low toxicity. It has been approved by the US Food and Drug Administration for being applied into adhesives as food packaging materials. p-Toluene sulfonamide is briefly called TSH and is commonly used for nickel plating. It can improve the coating structure by the adsorption on the electrode so that it has some degree of surface glossing effect; it is generally not strictly limited for the added amount of brighteners lax; moreover it also has very light effects on the coating characteristics. However, it can only give semi-bright coatings, and the surface gloss is related to the polishing quality of the matrix before plating. Currently, the brightener agents of nickel plating used is mostly some kinds of organic compounds. And the used amount of these organic compound, although are very little, but with a significant effect. In addition to brightening the coating, it can also largely determine the mechanical properties and chemical properties of the coating. But it must be realized that, since the bright nickel plating solution has been added to the organic brightener, it naturally makes the nickel plating layer contain a relative big amount of organic sulfur and other impurities, thus inevitably enlarging the internal stress, so its mechanical properties is a bitter lower than the conventional nickel-plate, and is prone to crack layer when the plating gets stress; its antirust ability is also worse than the dark nickel. Thus, a single layer of bright nickel is unable to improve the corrosion resistance and mechanical properties of the nickel layer; it must need to form a bi-layer and multilayer nickel or chromium to form a multilayer combination of decorative protective coatings. When toluene sulfonamide is heated to 105 °C, it will be decomposed and there will be nitrogen released (gas evolution 130 mL/g); p-toluene sulfonamide foaming agents can give a fine foaming with small product shrinkage. It also has a high tear strength and good stability. Thereby, it has a wide range of applications. The above information is edited by the lookchem of Dai xiongfeng.

Production methods

It is obtained by the reaction between toluenesulfonyl chloride and ammonia. First, add part of HN3 water into the reaction pot, stirring for adding p-toluenesulfonyl chloride with the temperature rising naturally to above 50 °C; after the temperature has dropped, add the remaining ammonia and have reaction for 0.5 h at 85~90 °C. Stop the reaction when the pH reaches 8 to 9. Cool to 20 °C, filter, and wash the filter cake with water to obtain the crude. Then further go through bleaching via activated carbon, alkali dissolution, acid precipitation, rejection filter, drying to get products.

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 4327, 1982 DOI: 10.1021/jo00143a031Synthetic Communications, 20, p. 293, 1990 DOI: 10.1080/00397919008052297Synthesis, p. 1031, 1986 DOI: 10.1055/s-1986-31862

Purification Methods

Crystallise the amide from hot water, then from EtOH or Et2O/pet ether. [Beilstein 11 H 104, 11 IV 376.]

Check Digit Verification of cas no

The CAS Registry Mumber 70-55-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 0 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 70-55:
(4*7)+(3*0)+(2*5)+(1*5)=43
43 % 10 = 3
So 70-55-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H9NO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H2,8,9,10)

70-55-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Alfa Aesar

  • (A12156)  p-Toluenesulfonamide, 98+%   

  • 70-55-3

  • 250g

  • 212.0CNY

  • Detail
  • Alfa Aesar

  • (A12156)  p-Toluenesulfonamide, 98+%   

  • 70-55-3

  • 500g

  • 257.0CNY

  • Detail
  • Alfa Aesar

  • (A12156)  p-Toluenesulfonamide, 98+%   

  • 70-55-3

  • 2500g

  • 1135.0CNY

  • Detail
  • Alfa Aesar

  • (A12156)  p-Toluenesulfonamide, 98+%   

  • 70-55-3

  • 10000g

  • 3820.0CNY

  • Detail
  • USP

  • (1672020)  p-Toluenesulfonamide  United States Pharmacopeia (USP) Reference Standard

  • 70-55-3

  • 1672020-200MG

  • 7,294.95CNY

  • Detail
  • Aldrich

  • (236330)  p-Toluenesulfonamide  ReagentPlus®, ≥99%

  • 70-55-3

  • 236330-10G

  • 322.92CNY

  • Detail
  • Aldrich

  • (236330)  p-Toluenesulfonamide  ReagentPlus®, ≥99%

  • 70-55-3

  • 236330-50G

  • 975.78CNY

  • Detail
  • Aldrich

  • (105902)  p-Toluenesulfonamide  reagent grade, 98%

  • 70-55-3

  • 105902-250G

  • 311.22CNY

  • Detail
  • Aldrich

  • (105902)  p-Toluenesulfonamide  reagent grade, 98%

  • 70-55-3

  • 105902-1KG

  • 738.27CNY

  • Detail
  • Vetec

  • (V900746)  p-Toluenesulfonamide  Vetec reagent grade, 98%

  • 70-55-3

  • V900746-250G

  • 53.82CNY

  • Detail

70-55-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name toluene-4-sulfonamide

1.2 Other means of identification

Product number -
Other names 4-methylbenzenesulfonamide

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:70-55-3 SDS

70-55-3Synthetic route

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With C36H55N2*Pd(2+)*C7H7NO2S(2-); hydrogen In benzene-d6 at 75℃; for 12h; Temperature; Time;100%
With iron(III) oxide; hydrazine hydrate In water at 120℃; for 1.5h; Inert atmosphere;99%
With D-glucose; potassium hydroxide In water at 85℃; for 0.0833333h; Green chemistry; chemoselective reaction;99%
N-(p-tolylsulfonyl)diphenyltellurimide
78727-83-0

N-(p-tolylsulfonyl)diphenyltellurimide

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

bis oxide
107590-68-1

bis oxide

Conditions
ConditionsYield
In diethyl ether; dichloromethane for 0.5h;A 78%
B 100%
N-(2,3-dimethylbut-2-enyl)-4-methylbenzenesulfonamide

N-(2,3-dimethylbut-2-enyl)-4-methylbenzenesulfonamide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 1h;100%
With triethylsilane; trifluoroacetic acid In dichloromethane for 1h;100%
triphenylphosphine
603-35-0

triphenylphosphine

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

N-p-tolylsulfonylphosphine imide
1058-14-6

N-p-tolylsulfonylphosphine imide

Conditions
ConditionsYield
With [(tris[2-{N-tetramethylguanidyl}ethyl]amine)CoII-[N-(p-toluenesulfonyl)imino](2-tert-butylsulfonyl)phenyliodinane](OTf)2 In acetone at -40℃; Kinetics; Reagent/catalyst; Time; Inert atmosphere;A n/a
B 100%
[N-(p-tolylsulfonyl)imino]phenyliodinane
55962-05-5

[N-(p-tolylsulfonyl)imino]phenyliodinane

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With 1,3-dihydroisobenzofuran; manganese(ll) chloride In acetonitrile at 20℃; for 12h; Reagent/catalyst; Inert atmosphere;100%
With iodine; benzene In dichloromethane at 20℃; for 24h; Mechanism; Inert atmosphere;99%
tetrahydroxy-1,4-quinone
319-89-1

tetrahydroxy-1,4-quinone

A

diphenyl telluride
1202-36-4

diphenyl telluride

B

hexaketocyclohexane
527-31-1

hexaketocyclohexane

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With N-(p-tolylsulfonyl)diphenyltellurimide In methanol for 0.5h; Ambient temperature;A 97%
B 88%
C 99%
diphenyl ditelluride
32294-60-3

diphenyl ditelluride

Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide
62486-35-5

Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide

A

bis(4-methoxyphenyl)telluride
4456-34-2

bis(4-methoxyphenyl)telluride

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

N,N-bis(phenyltelluro)-p-toluenesulfonamide
116161-54-7

N,N-bis(phenyltelluro)-p-toluenesulfonamide

Conditions
ConditionsYield
In chloroform for 5h; Ambient temperature;A 97%
B 98%
C 99%
Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide
62486-35-5

Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide

A

bis(4-methoxyphenyl)telluride
4456-34-2

bis(4-methoxyphenyl)telluride

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

N,N-bis(phenyltelluro)-p-toluenesulfonamide
116161-54-7

N,N-bis(phenyltelluro)-p-toluenesulfonamide

Conditions
ConditionsYield
With diphenyl ditelluride In chloroform Ambient temperature;A 97%
B 98%
C 99%
diphenyl-N-(p-toluenesulfonyl)selenimide
52867-19-3

diphenyl-N-(p-toluenesulfonyl)selenimide

thiophenol
108-98-5

thiophenol

A

diphenylselenide
1132-39-4

diphenylselenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In chloroform for 0.25h; Product distribution; Ambient temperature;A 96%
B 99%
C 97%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

thiophenol
108-98-5

thiophenol

A

dibenzyl selenide
1842-38-2

dibenzyl selenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In chloroform for 0.166667h; Product distribution; Ambient temperature;A 98%
B 99%
C 97%
diphenyl-N-(p-toluenesulfonyl)selenimide
52867-19-3

diphenyl-N-(p-toluenesulfonyl)selenimide

phenylmethanethiol
100-53-8

phenylmethanethiol

A

dibenzyl disulphide
150-60-7

dibenzyl disulphide

B

diphenylselenide
1132-39-4

diphenylselenide

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
In chloroform for 0.666667h; Product distribution; Ambient temperature;A 98%
B 97%
C 99%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

phenylmethanethiol
100-53-8

phenylmethanethiol

A

dibenzyl disulphide
150-60-7

dibenzyl disulphide

B

dibenzyl selenide
1842-38-2

dibenzyl selenide

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
In chloroform for 0.333333h; Product distribution; Ambient temperature;A 98%
B 99%
C 98%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

N,N-diphenylthiourea
102-08-9

N,N-diphenylthiourea

A

dibenzyl selenide
1842-38-2

dibenzyl selenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
ConditionsYield
In methanol for 0.5h; Mechanism; Ambient temperature;A 99%
B 98%
C 76%
para-thiocresol
106-45-6

para-thiocresol

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
Stage #1: para-thiocresol With dihydrogen peroxide; zirconium(IV) chloride In acetonitrile at 25℃;
Stage #2: With pyridine; ammonia In acetonitrile at 25℃; for 0.0333333h; chemoselective reaction;
99%
Stage #1: para-thiocresol With thionyl chloride; dihydrogen peroxide In water; acetonitrile at 25℃;
Stage #2: With pyridine; ammonia In water; acetonitrile at 25℃; for 0.0333333h;
97%
With tert.-butylhydroperoxide; ammonium hydroxide; iodine In water; acetonitrile at 100℃; for 16h;86%
N-formyl-N-tosylamide
4917-56-0

N-formyl-N-tosylamide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With hydrogenchloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In dichloromethane; water at 40℃; for 10h; Schlenk technique;99%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With ammonia; sodium hydrogencarbonate In water; acetone at 25℃; Schotten-Baumann Reaction; Flow reactor; Combinatorial reaction / High throughput screening (HTS);98%
With sodium isocyanate In water for 0.166667h; Reflux;97%
With ammonium hydroxide In tetrahydrofuran at 0 - 20℃;96%
tetrahydroxy-1,4-quinone
319-89-1

tetrahydroxy-1,4-quinone

A

rhodizonic acid
118-76-3

rhodizonic acid

B

bis(4-methoxyphenyl)telluride
4456-34-2

bis(4-methoxyphenyl)telluride

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide In methanol for 0.25h; Ambient temperature;A 89%
B 98%
C 98%
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

Sb,Sb,Sb-tripropyl-N-(p-tolylsulfonyl)stibine imide
80920-02-1

Sb,Sb,Sb-tripropyl-N-(p-tolylsulfonyl)stibine imide

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

bis(octafluoropentaloxy)tripropylantimony
80927-38-4

bis(octafluoropentaloxy)tripropylantimony

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 35 - 37℃;A 98%
B 83%
diphenyl ditelluride
32294-60-3

diphenyl ditelluride

N-(p-tolylsulfonyl)diphenyltellurimide
78727-83-0

N-(p-tolylsulfonyl)diphenyltellurimide

A

diphenyl telluride
1202-36-4

diphenyl telluride

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

N,N-bis(phenyltelluro)-p-toluenesulfonamide
116161-54-7

N,N-bis(phenyltelluro)-p-toluenesulfonamide

Conditions
ConditionsYield
In chloroform Ambient temperature;A 95%
B 96%
C 98%
N-[(4-methylphenyl)sulfonyl]-S,S-diphenyl-sulfilimine
13150-76-0

N-[(4-methylphenyl)sulfonyl]-S,S-diphenyl-sulfilimine

A

diphenyl sulfide
139-66-2

diphenyl sulfide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With sodium tetrahydroborate; meso-tetraphenylporphyrin iron(III) chloride In ethanol; benzene at 25℃; for 0.1h;A 98%
B n/a
C19H16N2O4S2
24698-06-4

C19H16N2O4S2

A

4-nitrophenyl phenyl sulfide
952-97-6

4-nitrophenyl phenyl sulfide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With 1-Benzyl-1,4-dihydronicotinamide; meso-tetraphenylporphyrin iron(III) chloride In benzene at 25℃; for 0.1h; NaBH4;A 98%
B n/a
In neat (no solvent) at 300℃; for 2h;
N-(p-tolylsulfonyl)diphenyltellurimide
78727-83-0

N-(p-tolylsulfonyl)diphenyltellurimide

A

diphenyl telluride
1202-36-4

diphenyl telluride

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

N,N-bis(phenyltelluro)-p-toluenesulfonamide
116161-54-7

N,N-bis(phenyltelluro)-p-toluenesulfonamide

Conditions
ConditionsYield
With diphenyl ditelluride In chloroform Ambient temperature;A 95%
B 96%
C 98%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

thiourea
17356-08-0

thiourea

A

CYANAMID
420-04-2

CYANAMID

B

dibenzyl selenide
1842-38-2

dibenzyl selenide

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
In methanol for 0.5h; Mechanism; Ambient temperature;A 72%
B 98%
C 98%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

benzenecarbothioamide
2227-79-4

benzenecarbothioamide

A

dibenzyl selenide
1842-38-2

dibenzyl selenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
In methanol for 0.5h; Mechanism; Ambient temperature;A 98%
B 98%
C 81%
C25H22NO2S2(1+)*ClO4(1-)

C25H22NO2S2(1+)*ClO4(1-)

A

diphenyl sulphone
127-63-9

diphenyl sulphone

B

S,S,S-triphenyloxosulfonium perchlorate

S,S,S-triphenyloxosulfonium perchlorate

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 1h; Ambient temperature;A 20%
B 77%
C 98%
di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
Stage #1: di(p-tolyl) disulfide With dihydrogen peroxide; zirconium(IV) chloride In acetonitrile at 25℃;
Stage #2: With pyridine; ammonia In acetonitrile at 25℃; for 0.0166667h; chemoselective reaction;
98%
N-(9-phenyl-9-fluorenyl)toluenesulfonamide
78388-16-6

N-(9-phenyl-9-fluorenyl)toluenesulfonamide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With chlorotriisopropylsilane; trifluoroacetic acid In dichloromethane for 0.25h;98%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

A

benzhydryl ether
574-42-5

benzhydryl ether

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With N-sulfinyl-p-toluenesulfonamide In diethyl ether at 25℃; for 20h;A 94%
B 97%
1,1-diphenylethanol
599-67-7

1,1-diphenylethanol

A

1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
In toluene for 20h; Heating;A 507 mg
B 97%
N-(p-tolylsulfonyl)(diacetylmethyl)-o-nitrophenylsulfimide

N-(p-tolylsulfonyl)(diacetylmethyl)-o-nitrophenylsulfimide

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

diacetylmethyl o-nitrophenyl sulfoxide
112128-28-6

diacetylmethyl o-nitrophenyl sulfoxide

Conditions
ConditionsYield
With sulfuric acid for 2h; Heating;A 97%
B 62%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide
18303-04-3

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;100%
With dmap; triethylamine In dichloromethane at 20℃;98%
With N,N,N',N'-tetramethylguanidinium acetate at 20℃; for 0.5h; Neat (no solvent);94%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-p-toluenesulfonylpyrrole
17639-64-4

N-p-toluenesulfonylpyrrole

Conditions
ConditionsYield
With phosphorus pentoxide In toluene at 110℃; for 0.333333h;100%
With scandium tris(trifluoromethanesulfonate) In 1,4-dioxane at 100℃; for 0.666667h; Clauson-Kaas condensation;95%
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h;90%
1,8-bis(p-toluenesulfonyloxy)-3,6-bis(p-toluenesulfonyl)-3,6-diazaoctane
56234-52-7

1,8-bis(p-toluenesulfonyloxy)-3,6-bis(p-toluenesulfonyl)-3,6-diazaoctane

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N,N',N-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane
52667-89-7

N,N',N-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 240h; Cyclization; Heating;100%
With potassium carbonate In acetonitrile for 144h; Heating;97%
benzaldehyde
100-52-7

benzaldehyde

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

isopropenylbenzene
98-83-9

isopropenylbenzene

N-(1,3-diphenylbut-3-en-1-yl)-4-methylbenzenesulfonamide
258851-74-0

N-(1,3-diphenylbut-3-en-1-yl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; ytterbium(III) triflate In tetrahydrofuran; dichloromethane at 20℃; for 1h;100%
With trimethylsilyl trifluoromethanesulfonate; ytterbium(III) triflate In tetrahydrofuran; dichloromethane at 20℃; for 1h;92%
With trimethylsilyl trifluoromethanesulfonate; ytterbium(III) triflate In tetrahydrofuran; dichloromethane at 20℃; for 1h; Condensation; imino ene reaction;90%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N,N-Dimethyl-N'-<(4-methylphenyl)sulfonyl>formamidine

N,N-Dimethyl-N'-<(4-methylphenyl)sulfonyl>formamidine

Conditions
ConditionsYield
In dichloromethane for 0.5h; Heating;100%
diphenylmethylenecyclopropene
7632-57-7

diphenylmethylenecyclopropene

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N,N-bis-(2-benzhydryl-allyl)-4-methyl-benzenesulfonamide

N,N-bis-(2-benzhydryl-allyl)-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
With palladium diacetate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In toluene at 110℃; for 3h;100%
bis(p-methoxyphenyl)methylenecyclopropane
28228-81-1

bis(p-methoxyphenyl)methylenecyclopropane

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N,N-bis-{2-[bis-(4-methoxy-phenyl)-methyl]-allyl}-4-methyl-benzenesulfonamide

N,N-bis-{2-[bis-(4-methoxy-phenyl)-methyl]-allyl}-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
With palladium diacetate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In toluene at 115℃; for 3h;100%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

methylheptylmethylenecyclopropane

methylheptylmethylenecyclopropane

4-methyl-N,N-bis-[2-(1-methyl-octyl)-allyl]-benzenesulfonamide

4-methyl-N,N-bis-[2-(1-methyl-octyl)-allyl]-benzenesulfonamide

Conditions
ConditionsYield
With palladium diacetate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In toluene at 110℃; for 8h;100%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

N,N-diphenyl-p-toluenesulfonamide
4703-19-9

N,N-diphenyl-p-toluenesulfonamide

Conditions
ConditionsYield
With cesium fluoride In acetonitrile at 20℃; for 24h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(benzylidene)-p-methylbenzenesulfonamide
51608-60-7

N-(benzylidene)-p-methylbenzenesulfonamide

Conditions
ConditionsYield
at 170℃;100%
at 170℃;95%
at 180℃; for 0.75h;91%
at 120 - 130℃; for 4h;82%
at 150℃; for 2h;
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(4-fluorobenzylidene)-4-methylbenzenesulfonamide
193675-43-3

N-(4-fluorobenzylidene)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With Amberlyst(R) 15 ion-exchange resin In toluene for 16h; Inert atmosphere; Reflux; Molecular sieve;100%
With amberlyst 15 In toluene for 16h; Heating; Molecular sieve;98%
With Amberlyst 15 In toluene for 12h; Molecular sieve; Reflux; Dean-Stark;98%
2-Phenylbenzaldehyde
1203-68-5

2-Phenylbenzaldehyde

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(2-phenylbenzylidene)-4-methylbenzenesulfonamide
1292302-62-5

N-(2-phenylbenzylidene)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With boron trichloride - methyl sulfide complex In toluene at 20℃; for 7.5h;100%
With copper diacetate In toluene Reflux;97%
With tetraethoxy orthosilicate Heating;47%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

hept-6-en-1-yl 4-methylbenzenesulfonate
110046-51-0

hept-6-en-1-yl 4-methylbenzenesulfonate

N-(hept-6-en-1-yl)-4-methylbenzenesulfonamide
1353723-21-3

N-(hept-6-en-1-yl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 15h; Inert atmosphere; Reflux;100%
3-(trifluoromethyl)dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate
1469876-14-9

3-(trifluoromethyl)dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

9-tosyl-2-(trifluoromethyl)-9H-carbazole
1469876-08-1

9-tosyl-2-(trifluoromethyl)-9H-carbazole

Conditions
ConditionsYield
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol at 90℃; for 16h; Inert atmosphere;100%
With copper diacetate; sodium carbonate; ethylene glycol In isopropyl alcohol at 85℃; for 16h; Ullmann Condensation; Inert atmosphere;55%
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol for 16h; Inert atmosphere; Reflux; Green chemistry;
[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
189999-35-7

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

9-tosyl-9H-carbazole
3165-71-7

9-tosyl-9H-carbazole

Conditions
ConditionsYield
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol at 90℃; for 16h; Inert atmosphere;100%
With copper diacetate; sodium carbonate; ethylene glycol In isopropyl alcohol at 85℃; for 16h; Ullmann Condensation; Inert atmosphere;60%
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol for 16h; Inert atmosphere; Reflux; Green chemistry;
nonan-1-al
124-19-6

nonan-1-al

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-octylidene-p-toluenesulfonamide

N-octylidene-p-toluenesulfonamide

Conditions
ConditionsYield
With anthranilic acid In dichloromethane at 60℃; for 24h; Molecular sieve;100%
estragole oxide
51410-45-8

estragole oxide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(2-hydroxy-3-(4-methoxyphenyl)propyl)-4-methylbenzenesulfonamide

N-(2-hydroxy-3-(4-methoxyphenyl)propyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 90℃; for 6h;100%
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 90℃; for 5h;98%
diethylphosphonoacetic acid
3095-95-2

diethylphosphonoacetic acid

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

2-(diethoxyphosphoryl)-N-(p-toluenesulfonyl)ethanamide

2-(diethoxyphosphoryl)-N-(p-toluenesulfonyl)ethanamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 71h; Inert atmosphere;100%
4-methyl-1,2-dihydronaphthalene
4373-13-1

4-methyl-1,2-dihydronaphthalene

benzaldehyde
100-52-7

benzaldehyde

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(2-(3,4-dihydronaphthalen-1-yl)-1-phenylethyl)-4-methylbenzenesulfonamide

N-(2-(3,4-dihydronaphthalen-1-yl)-1-phenylethyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; ytterbium(III) triflate In tetrahydrofuran; dichloromethane at 20℃; for 0.0166667h;100%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-d2-p-toluenesulfonamide

N-d2-p-toluenesulfonamide

Conditions
ConditionsYield
With deuteromethanol for 5h; Sealed tube; Inert atmosphere;100%
1-acetoxy-1,2-benziodoxol-3-one
1829-26-1

1-acetoxy-1,2-benziodoxol-3-one

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Zhdankin’s reagent

Zhdankin’s reagent

Conditions
ConditionsYield
Stage #1: 1-acetoxy-1,2-benziodoxol-3-one With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: toluene-4-sulfonamide In dichloromethane at 20℃; for 3h; Inert atmosphere;
100%
1-(2-methoxyphenyl)ethanol
13513-82-1

1-(2-methoxyphenyl)ethanol

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

A

N-(1-(2-methoxyphenyl)ethyl)-4-methylbenzenesulfonamide
93027-83-9

N-(1-(2-methoxyphenyl)ethyl)-4-methylbenzenesulfonamide

B

di[1-(2-methoxyphenyl)ethyl]ether
859312-83-7

di[1-(2-methoxyphenyl)ethyl]ether

Conditions
ConditionsYield
With acidic mesoporous zeolite β-catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Sealed tube; Inert atmosphere;A 100%
B n/a
α-methyl-4-(methylthio)benzenemethanol
32293-73-5

α-methyl-4-(methylthio)benzenemethanol

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

A

1-(4-methylthiophenyl)-1-(p-toluenesulfonamido)ethane

1-(4-methylthiophenyl)-1-(p-toluenesulfonamido)ethane

B

C18H22OS2

C18H22OS2

Conditions
ConditionsYield
With acidic mesoporous zeolite β-catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Sealed tube; Inert atmosphere;A 100%
B n/a
4,4'-dimethylbenzhydrol
885-77-8

4,4'-dimethylbenzhydrol

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

A

bis[bis(p-tolyl)methyl] ether
37858-01-8

bis[bis(p-tolyl)methyl] ether

B

C22H23NO2S
1581274-94-3

C22H23NO2S

Conditions
ConditionsYield
With acidic mesoporous zeolite β-catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Sealed tube; Inert atmosphere;A n/a
B 100%
4,4'-dimethoxychalcone
2373-89-9

4,4'-dimethoxychalcone

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

2-bromo-1-(4'-methoxyphenyl)-3-(4-methoxyphenyl)-3-(p-toluenesulfonamido)propan-1-one

2-bromo-1-(4'-methoxyphenyl)-3-(4-methoxyphenyl)-3-(p-toluenesulfonamido)propan-1-one

Conditions
ConditionsYield
With N-Bromosuccinimide; aluminium In dichloromethane at 25℃; for 0.166667h; regioselective reaction;99.8%
With N-Bromosuccinimide; silicon In dichloromethane at 25℃; for 1h; Aerobic conditions; stereoselective reaction;98%
With N-Bromosuccinimide; copper In dichloromethane at 25℃; for 1h; stereoselective reaction;97.5%
With N-Bromosuccinimide; potassium iodide In dichloromethane at 25℃; for 2h; Aerobic conditions; regioselective reaction;97%

70-55-3Relevant articles and documents

Cellular AND Gates: Synergistic Recognition to Boost Selective Uptake of Polymeric Nanoassemblies

Fernandez, Ann,Gao, Jingjing,Thayumanavan, S.,Wu, Peidong,Zhuang, Jiaming

, p. 10456 - 10460 (2020)

The development of nanoparticle-based biomedical applications has been hampered due to undesired off-target effects. Herein, we outline a cellular AND gate to enhance uptake selectivity, in which a nanoassembly–cell interaction is turned on, only in the concurrent presence of two different protein functions, an enzymatic reaction (alkaline phosphatase, ALP) and a ligand–protein (carbonic anhydrase IX, CA IX) binding event. Selective uptake of nanoassemblies was observed in cells that overexpress both of these proteins (unicellular AND gate). Interestingly, selective uptake can also be achieved in CA IX overexpressed cells, when cocultured with ALP overexpressed cells, where the nanoassembly presumably acts as a mediator for cell–cell communication (bicellular AND gate). This logic-gated cellular uptake could find use in applications such as tumor imaging or theranostics.

Kinetics and Mechanism of Oxidation of L-Threonine in Acid Media by Sodium N-Chloro-p-toluenesulfonamide

Mahadevappa, D. S.,Rangappa, K. S.,Gowda, N. M. M.,Gowda, B. Thimme

, p. 3651 - 3658 (1981)

Kinetics of oxidation of L-threonine in the presence of HCl, HClO4, and H2SO4 by chloramine-T (CAT) has been investigated at 35 deg C.The reactions follow identical kinetics in all acids, being first order in CAT, fractional order in substrate and Cl- ion, and of an inverse fractional order in +>.Variation of ionic strength and addition of the reaction product, p-toluenesulfonamide, or the ions SO42- and ClO4- had no effect on the rate.Decrease of dielectric constant of the medium by adding methanol decreased the rate.The solvent isotope effect was studied by using heavy water.The reactions were studied at different temperatures, and activation parameters have been computed.Mechanisms proposed and the derived rate laws are consistent with the observed kinetics.The rate constants predicted by the derived rate laws, as the concentrations of H+ ion, substrate, and Cl- ion change, are in excellent agreement with the observed rate constants, thus further justifying these rate laws and hence the proposed mechanistic schemes.

Synthesis of 8-Alkoxy-5 H-isochromeno[3,4- c]isoquinolines and 1-Alkoxy-4-arylisoquinolin-3-ols through Rh(III)-Catalyzed C-H Functionalization of Benzimidates with 4-Diazoisochroman-3-imines and 4-Diazoisoquinolin-3-ones

Li, Zhenmin,Lu, Ping,Wang, Yanguang,Xie, Jianwei

, p. 5525 - 5535 (2020)

Rh(III)-catalyzed C-H activation/annulation of benzimidates with 4-diazoisochroman-3-imines furnished 8-alkoxy-5H-isochromeno[3,4-c]isoquinolines in moderate to excellent yields with a broad range of substrate scope. The reaction was carried out under mild reaction conditions and could be scaled up with practical usage. Similar reaction between benzimidates and 4-diazoisoquinolin-3-ones provided 1-alkoxy-4-arylisoquinolin-3-ols in excellent yields. Moreover, the synthesized products could be conveniently transformed to the corresponding heterocycles with a 1,8-naphthyridinone or isochromenopyridinone core, which are privileged structures in medicinal chemistry.

Kinetics and Mechanism of the Oxidation of Hypophospite with N-Chlorotoluene-p-sulphonamide (Chloramine T) catalysed by Osmium(VIII) in Alkaline Solution

Hussain, Juzar,Mishra, Som Kant,Sharma, Preen Dutt

, p. 89 - 92 (1991)

The kinetics of osmium(VIII)-catalysed oxidation of hypophosphite, H2PO2-, with chloramine T (cat, N-chlorotoluene-p-sulphamide) was studied by estimating the latter iodometrically.The rate law (i) holds for -> = 0.02-0.142, H2PO

Anisole alkylation with N-arenesulfonylimines of dichloro(phenyl)acetaldehyde and derivatives thereof

Drozdova,Mirskova

, p. 819 - 821 (2001)

N-[1-4-Methoxyphenyl-2-phenyl-2,2-dichloroethyl]arenesulfonamides are formed in reaction of N-(2-phenyl-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-phenyl-2,2-dichloroethylidene)-4-methylbenzenesulfonamide with anisole catalyzed by boron t

The Reaction of Thiocumulenes with Fulvene

Saito, Takao,Musashi, Teruhiko,Motoki, Shinichi

, p. 3377 - 3378 (1980)

S-(9-Fluorenylidene)-N-(p-tolylsulfonyl)-sulfimide and bis(p-tolylsulfonyl)sulfur diimide reacted as 1,3-dipoles with fulvenes to form (2+3)cycloadducts.

Structural, vibrational spectra and normal coordinate analysis for two tautomers of 4(5)-(2′-furyl)-imidazole

Ledesma,Zinczuk,Gonzalez, J.J. Lopez,Altabef, A. Ben,Brandan

, p. 587 - 597 (2010)

We have synthesized both the 4 and 5 tautomeric forms of 4(5)-(2′-furyl)-imidazole (1) and investigated their molecular vibrations by infrared and Raman spectroscopies as well as by calculation based on the density functional theory (DFT) approach. Examination of the temperature dependence of IR intensity revealed the band characteristics of the 4 and 5 tautomersof(1).Comparisonofexperimentalandcalculatedchemicalshiftsinnucl earmagneticresonance(NMR)spectroscopy was made in order to identify the two tautomeric forms. The assignment of vibrational normal modes was performed, and the forcefieldobtainedreproduced theexperimentalvibrationalwavenumbers with a root mean-squaredeviation (RMSD)value of ca. 13 cm-1 for both tautomers. The natural bond orbital (NBO) study reveals the characteristics of the electronic delocalization of the two tautomeric structures.

Synthesis of cyclic sulfonamides via Pd-catalyzed intramolecular coupling reaction: An expedient approach to polycyclic sultams

Majumdar,Mondal, Shovan,De, Nirupam

, p. 2851 - 2855 (2008)

A divergent synthetic approach to polycyclic sultams utilizing intramolecular ligand-free intramolecular coupling reaction is described. Georg Thieme Verlag Stuttgart.

Formation and Isolation of the Disulphide Dication of 1,5-Dithiacyclo-octane in the Reactions of the Corresponding S-Oxide and S-(N-tosylimide) in Concentrated Sulphuric Acid

Furukawa, Naomichi,Kawada, Akira,Kawai, Tsutomu

, p. 1151 - 1152 (1984)

The disulphide dication of 1,5-dithiacyclo-octane was generated in the reaction of the corresponding S-oxide and S-(N-tosylimide) with conc.H2SO4 and isolated in crystalline form.

Michael additions of oxygen and sulfur nucleophiles to 3,4-Di-t-butyl-1-[(p-tolyl)sulfonylimino]-1,1-dihydrothiophene. A comparison study with 3,4-Di-t-butylthiophene 1-oxide and 1,1-dioxide

Otani, Takashi,Sugihara, Yoshiaki,Ishii, Akihiko,Nakayama, Juzo

, p. 744 - 745 (2000)

The reactions of 3,4-di-t-butyl-1-[(p-tolyl)sulfonylimino]-1,1-dihydrothiophene with RONa and RSNa furnished 2-alkoxy-and 2-alkylthio-substituted thiophenes, respectively, through Michael adduct formation. The reaction of 3,4-di-t-butylthiophene 1-oxide with RSNa gave 1,6-Michael adducts, whereas the corresponding reaction of 3,4-di-t-butylthiophene 1,1-dioxide produced a mixture of 1,4-and 1,6-adducts.

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