2, 4, 4, 6-Tetrabromo-2, 5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS) and bromine as efficient catalysts for dithioacetalization and oxathioacetalization of …

N Iranpoor, H Firouzabadi, HR Shaterian…

Index: Iranpoor, Nasser; Firouzabadi, Habib; Shaterian, Hamid Reza; Zolfigol Phosphorus, Sulfur and Silicon and Related Elements, 2002 , vol. 177, # 5 p. 1047 - 1071

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Citation Number: 6

Abstract

The use of 2, 4, 4, 6-tetrabromo-2, 5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1, 3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high yields in the ...

 Related Synthetic Route
Benzene,1-(diethoxymethyl)-2-methyl- Structure

5469-00-1

Benzene,1-(diet...

1,2-Ethanedithiol Structure

540-63-6

1,2-Ethanedithiol

~90%

2-(o-Tolyl)-1,3-dithiolane Structure

67810-92-8

2-(o-Tolyl)-1,3...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

3-methoxybenzaldoxime Structure

38489-80-4

3-methoxybenzal...

~91%

2-(3-methoxyphenyl)-1,3-dithiane Structure

54308-43-9

2-(3-methoxyphe...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

1-Morpholino-1-cyclohexene Structure

670-80-4

1-Morpholino-1-...

~93%

1,5-Dithiaspiro[5.5]undecane Structure

180-96-1

1,5-Dithiaspiro...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

Cyclohexanone oxime Structure

100-64-1

Cyclohexanone oxime

~86%

1,5-Dithiaspiro[5.5]undecane Structure

180-96-1

1,5-Dithiaspiro...

Acetophenone diethyl ketal Structure

4316-37-4

Acetophenone di...

1,2-Ethanedithiol Structure

540-63-6

1,2-Ethanedithiol

~86%

2-methyl-2-phenyl-1,3-dithiolane Structure

5769-02-8

2-methyl-2-phen...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

butylidene-propyl-amine Structure

7707-71-3

butylidene-prop...

~92%

2-propyl-1,3-dithiane Structure

42196-80-5

2-propyl-1,3-di...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

Benzaldehyde,4-methyl-, oxime Structure

3235-02-7

Benzaldehyde,4-...

~92%

2-(p-Tolyl)-1,3-dithiane Structure

56637-44-6

2-(p-Tolyl)-1,3...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

4-MeO(C6H4)CH(OAc)2 Structure

14202-31-4

4-MeO(C6H4)CH(OAc)2

~90%

4-Methoxybenzaldehyde trimethylenedithioacetal Structure

24588-72-5

4-Methoxybenzal...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

N/A Structure

55605-27-1

N/A

~93%

2-(4-bromophenyl)-1,3-dithiane Structure

58928-91-9

2-(4-bromopheny...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

2,2-diphenyl-1,3-dioxane Structure

786-03-8

2,2-diphenyl-1,...

~82%

2,2-diphenyl-1,3-dithiane Structure

10359-08-7

2,2-diphenyl-1,...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

Benzophenone oxime Structure

574-66-3

Benzophenone oxime

~50%

2,2-diphenyl-1,3-dithiane Structure

10359-08-7

2,2-diphenyl-1,...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

4-Chlorobenzenecarbaldehyde oxime Structure

3848-36-0

4-Chlorobenzene...

~91%

2-(4-chlorophenyl)-1,3-dithiane Structure

10359-09-8

2-(4-chlorophen...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

(E)-2-(2-phenylethenyl)-1,4-dioxolane Structure

83977-12-2

(E)-2-(2-phenyl...

~88%

2-(2-phenylethenyl)-1,3-dithiane Structure

26958-41-8

2-(2-phenylethe...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

acetic acid,3-phenylprop-2-ene-1,1-diol Structure

64847-78-5

acetic acid,3-p...

~91%

2-(2-phenylethenyl)-1,3-dithiane Structure

26958-41-8

2-(2-phenylethe...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

3-Phenyl-prop-2-enal oxime Structure

13372-81-1

3-Phenyl-prop-2...

~90%

2-(2-phenylethenyl)-1,3-dithiane Structure

26958-41-8

2-(2-phenylethe...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

1,3-Dioxolane,2-(4-nitrophenyl)- Structure

2403-53-4

1,3-Dioxolane,2...

~90%

1,3-Dithiane,2-(4-nitrophenyl)- Structure

24588-74-7

1,3-Dithiane,2-...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

3,9-bis(4-nitrophenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane Structure

59147-86-3

3,9-bis(4-nitro...

~90%

1,3-Dithiane,2-(4-nitrophenyl)- Structure

24588-74-7

1,3-Dithiane,2-...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

Methanediol,1-(4-nitrophenyl)-, 1,1-diacetate Structure

2929-91-1

Methanediol,1-(...

~92%

1,3-Dithiane,2-(4-nitrophenyl)- Structure

24588-74-7

1,3-Dithiane,2-...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

2-(2-methylphenyl)-1,3-dioxolane Structure

64380-54-7

2-(2-methylphen...

~88%

2-(2-methylphenyl)-1,3-dithiane Structure

56637-46-8

2-(2-methylphen...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

2-methylbenzaldehyde oxime Structure

14683-79-5

2-methylbenzald...

~91%

2-(2-methylphenyl)-1,3-dithiane Structure

56637-46-8

2-(2-methylphen...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

3,9-di(o-chlorophenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane Structure

35583-08-5

3,9-di(o-chloro...

~90%

2-(2-chlorophenyl)-1,3-dithiane Structure

69849-09-8

2-(2-chlorophen...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

1-Chloro-2-(diethoxymethyl)benzene Structure

35364-86-4

1-Chloro-2-(die...

~93%

2-(2-chlorophenyl)-1,3-dithiane Structure

69849-09-8

2-(2-chlorophen...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

o-chlorobenzaldoxime Structure

3717-28-0

o-chlorobenzaldoxime

~88%

2-(2-chlorophenyl)-1,3-dithiane Structure

69849-09-8

2-(2-chlorophen...

Benzene,1-(diethoxymethyl)-4-nitro- Structure

2403-62-5

Benzene,1-(diet...

mercaptoethanol Structure

60-24-2

mercaptoethanol

~89%

4-nitrophenyl-1,3-oxathiolane Structure

22391-06-6

4-nitrophenyl-1...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

3,9-dimethyl-3,9-diphenyl-2,4,8,10-tetraoxaspiro[5.5]undecane Structure

110954-16-0

3,9-dimethyl-3,...

~92%

1,3-Dithiane,2-methyl-2-phenyl- Structure

6331-22-2

1,3-Dithiane,2-...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

N/A Structure

14990-66-0

N/A

~90%

1,3-Dithiane,2-methyl-2-phenyl- Structure

6331-22-2

1,3-Dithiane,2-...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

Ethanone, 1-phenyl-,2-phenylhydrazone Structure

583-11-9

Ethanone, 1-phe...

~88%

1,3-Dithiane,2-methyl-2-phenyl- Structure

6331-22-2

1,3-Dithiane,2-...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

4-(1-phenylethenyl)morpholine Structure

7196-01-2

4-(1-phenylethe...

~88%

1,3-Dithiane,2-methyl-2-phenyl- Structure

6331-22-2

1,3-Dithiane,2-...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

Acetophenone oxime Structure

613-91-2

Acetophenone oxime

~70%

1,3-Dithiane,2-methyl-2-phenyl- Structure

6331-22-2

1,3-Dithiane,2-...

1,1'-(Diethoxymethylene)dibenzene Structure

6397-77-9

1,1'-(Diethoxym...

1,2-Ethanedithiol Structure

540-63-6

1,2-Ethanedithiol

~72%

1,3-DITHIOLANE, 2,2-DIPHENYL- Structure

6317-10-8

1,3-DITHIOLANE,...

3-methoxybenzaldehyde diethyl acetal Structure

2403-47-6

3-methoxybenzal...

1,2-Ethanedithiol Structure

540-63-6

1,2-Ethanedithiol

~92%

1,3-DITHIOLANE, 2-(m-METHOXYPHENYL)- Structure

82436-19-9

1,3-DITHIOLANE,...

Cinnamaldehyde, diethyl acetal Structure

7148-78-9

Cinnamaldehyde,...

mercaptoethanol Structure

60-24-2

mercaptoethanol

~89%

2-(2-phenylethenyl)-1,3-oxathiolane Structure

80563-94-6

2-(2-phenylethe...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

Methanediol,1-(1-naphthalenyl)-, 1,1-diacetate Structure

64002-53-5

Methanediol,1-(...

~89%

2-naphthalen-1-yl-1,3-dithiane Structure

57009-77-5

2-naphthalen-1-...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

1,3-Dioxane,2-methyl-2-(phenylmethyl)- Structure

6413-86-1

1,3-Dioxane,2-m...

~84%

2-benzyl-2-methyl-1,3-dithiane Structure

5849-03-6

2-benzyl-2-meth...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

2,2-diethoxypropylbenzene Structure

71094-32-1

2,2-diethoxypro...

~90%

2-benzyl-2-methyl-1,3-dithiane Structure

5849-03-6

2-benzyl-2-meth...

1,3-Propanedithiol Structure

109-80-8

1,3-Propanedithiol

(2,4-dimethoxyphenyl)methylene diacetate Structure

173282-52-5

(2,4-dimethoxyp...

~87%

2-(2,4-dimethoxyphenyl)-1,3-dithiane Structure

135655-77-5

2-(2,4-dimethox...


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