Journal of the American Chemical Society

Intramolecular generation of oxonium ylides from functionalized arylcarbenes

W Kirmse, K Kund

Index: Kirmse, Wolfgang; Kund, Klaus Journal of the American Chemical Society, 1989 , vol. 111, # 4 p. 1465 - 1473

Full Text: HTML

Citation Number: 29

Abstract

Abstract: Arylcarbenes carrying alkoxyalkyl groups in the ortho position have been generated by flash pyrolysis and photolysis of appropriate tosylhydrazone sodium salts. In the gas phase and in aprotic solvents, interaction of the carbenes with the lone electron pairs of oxygen competes efficiently with insertion into CH bonds. Both five-and six- membered cyclic oxonium ylides have been generated. The ylides 23, 37, 61b, and 74 ...

 Related Synthetic Route
Methanol Structure

67-56-1

Methanol

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

119367-60-1

2-(Methoxymethy...

~%

Phthalane Structure

496-14-0

Phthalane

N/A Structure

15018-12-9

N/A

Detail Learn More
diglyme Structure

111-96-6

diglyme

sodium 2-(2-(methoxymethyl)benzylidene)-1-tosylhydrazin-1-ide Structure

119391-23-0

sodium 2-(2-(me...

~%

Phthalane Structure

496-14-0

Phthalane

Isochroman Structure

493-05-0

Isochroman

Detail Learn More
sodium 2-(2-(methoxymethyl)benzylidene)-1-tosylhydrazin-1-ide Structure

119391-23-0

sodium 2-(2-(me...

~%

Phthalane Structure

496-14-0

Phthalane

Isochroman Structure

493-05-0

Isochroman

α-methoxy-α,α'-dihydrobenzocyclobutene Structure

36101-23-2

α-methoxy-α,α'-...

Detail Learn More
Methanol Structure

67-56-1

Methanol

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

119367-60-1

2-(Methoxymethy...

~%

Phthalane Structure

496-14-0

Phthalane

Isochroman Structure

493-05-0

Isochroman

Detail Learn More
Phthalide Structure

87-41-2

Phthalide

~%

Benzyl methyl ether Structure

538-86-3

Benzyl methyl ether

Learn More
2-((Benzyloxy)methyl)benzyl alcohol Structure

119367-90-7

2-((Benzyloxy)m...

~%

Benzyl methyl ether Structure

538-86-3

Benzyl methyl ether

Learn More
2-(Phenylmethoxymethyl)benzaldehyde Structure

119367-65-6

2-(Phenylmethox...

~%

Benzyl methyl ether Structure

538-86-3

Benzyl methyl ether

Learn More
2-[(Benzyloxy)methyl]benzoic acid Structure

119367-89-4

2-[(Benzyloxy)m...

~%

Benzyl methyl ether Structure

538-86-3

Benzyl methyl ether

Learn More
N/A Structure

119367-88-3

N/A

~%

Benzyl methyl ether Structure

538-86-3

Benzyl methyl ether

Learn More
N'-(2-((benzyloxy)methyl)benzylidene)-4-methylbenzenesulfonohydrazide Structure

119367-66-7

N'-(2-((benzylo...

~%

Benzyl methyl ether Structure

538-86-3

Benzyl methyl ether

Phthalane Structure

496-14-0

Phthalane

N/A Structure

119367-68-9

N/A

Detail Learn More
N'-(2-((benzyloxy)methyl)benzylidene)-4-methylbenzenesulfonohydrazide Structure

119367-66-7

N'-(2-((benzylo...

~%

Benzyl methyl ether Structure

538-86-3

Benzyl methyl ether

Phthalane Structure

496-14-0

Phthalane

3-phenyl-3,4-dihydro-1H-isochromene Structure

29539-18-2

3-phenyl-3,4-di...

Detail Learn More
Methanol Structure

67-56-1

Methanol

N'-(2-((benzyloxy)methyl)benzylidene)-4-methylbenzenesulfonohydrazide Structure

119367-66-7

N'-(2-((benzylo...

~%

Benzyl methyl ether Structure

538-86-3

Benzyl methyl ether

Phthalane Structure

496-14-0

Phthalane

Detail Learn More
Methanol Structure

67-56-1

Methanol

N'-(2-((benzyloxy)methyl)benzylidene)-4-methylbenzenesulfonohydrazide Structure

119367-66-7

N'-(2-((benzylo...

~%

Benzyl methyl ether Structure

538-86-3

Benzyl methyl ether

Phthalane Structure

496-14-0

Phthalane

Detail Learn More
sodium 2-(2-((benzyloxy)methyl)benzylidene)-1-tosylhydrazin-1-ide Structure

119391-25-2

sodium 2-(2-((b...

~%

3-phenyl-3,4-dihydro-1H-isochromene Structure

29539-18-2

3-phenyl-3,4-di...

2-PHENETHYLBENZALDEHYDE Structure

32832-96-5

2-PHENETHYLBENZ...

N/A Structure

119367-68-9

N/A

Detail Learn More
sodium 2-(2-((benzyloxy)methyl)benzylidene)-1-tosylhydrazin-1-ide Structure

119391-25-2

sodium 2-(2-((b...

~%

3-phenyl-3,4-dihydro-1H-isochromene Structure

29539-18-2

3-phenyl-3,4-di...

2-PHENETHYLBENZALDEHYDE Structure

32832-96-5

2-PHENETHYLBENZ...

N/A Structure

119367-68-9

N/A

Detail Learn More
sodium 2-(2-((benzyloxy)methyl)benzylidene)-1-tosylhydrazin-1-ide Structure

119391-25-2

sodium 2-(2-((b...

~%

3-phenyl-3,4-dihydro-1H-isochromene Structure

29539-18-2

3-phenyl-3,4-di...

2-PHENETHYLBENZALDEHYDE Structure

32832-96-5

2-PHENETHYLBENZ...

Bibenzyl Structure

103-29-7

Bibenzyl

Detail Learn More
sodium 2-(2-((benzyloxy)methyl)benzylidene)-1-tosylhydrazin-1-ide Structure

119391-25-2

sodium 2-(2-((b...

~%

3-phenyl-3,4-dihydro-1H-isochromene Structure

29539-18-2

3-phenyl-3,4-di...

2-PHENETHYLBENZALDEHYDE Structure

32832-96-5

2-PHENETHYLBENZ...

Bibenzyl Structure

103-29-7

Bibenzyl

Detail Learn More
Methanol Structure

67-56-1

Methanol

N'-(2-((benzyloxy)methyl)benzylidene)-4-methylbenzenesulfonohydrazide Structure

119367-66-7

N'-(2-((benzylo...

~%

Benzyl methyl ether Structure

538-86-3

Benzyl methyl ether

Phthalane Structure

496-14-0

Phthalane

Detail Learn More
Benzenemethanol, 2-(methoxymethyl)- (9CI) Structure

62172-88-7

Benzenemethanol...

~75%

2-(methoxymethyl)benzaldehyde Structure

106020-70-6

2-(methoxymethy...

Learn More
Isochroman-1-one Structure

4702-34-5

Isochroman-1-one

~%

1-bromo-3,4-dihydro-1H-isochromene Structure

50683-32-4

1-bromo-3,4-dih...

Learn More
N/A Structure

119367-94-1

N/A

~%

1-bromo-3,4-dihydro-1H-isochromene Structure

50683-32-4

1-bromo-3,4-dih...

Learn More
N/A Structure

119367-93-0

N/A

~%

1-bromo-3,4-dihydro-1H-isochromene Structure

50683-32-4

1-bromo-3,4-dih...

Learn More
2-(2-(Benzyloxy)ethyl)benzoic acid Structure

119367-92-9

2-(2-(Benzyloxy...

~%

1-bromo-3,4-dihydro-1H-isochromene Structure

50683-32-4

1-bromo-3,4-dih...

Learn More
2-(2-(Benzyloxy)ethyl)benzaldehyde tosylhydrazone Structure

119367-95-2

2-(2-(Benzyloxy...

~%

1-bromo-3,4-dihydro-1H-isochromene Structure

50683-32-4

1-bromo-3,4-dih...

Learn More
Benzenemethanol, 2-(2-methoxyethyl) Structure

119367-72-5

Benzenemethanol...

~%

1-bromo-3,4-dihydro-1H-isochromene Structure

50683-32-4

1-bromo-3,4-dih...

Learn More
N/A Structure

119367-73-6

N/A

~%

1-bromo-3,4-dihydro-1H-isochromene Structure

50683-32-4

1-bromo-3,4-dih...

Learn More
N/A Structure

119367-78-1

N/A

~%

1-bromo-3,4-dihydro-1H-isochromene Structure

50683-32-4

1-bromo-3,4-dih...

Learn More
N/A Structure

119367-74-7

N/A

~%

1-bromo-3,4-dihydro-1H-isochromene Structure

50683-32-4

1-bromo-3,4-dih...

Learn More
N/A Structure

119391-26-3

N/A

~%

1-bromo-3,4-dihydro-1H-isochromene Structure

50683-32-4

1-bromo-3,4-dih...

Learn More
N/A Structure

119367-78-1

N/A

~8%

Isochroman Structure

493-05-0

Isochroman

N/A Structure

119367-77-0

N/A

Learn More
N/A Structure

119367-94-1

N/A

~%

Isochroman Structure

493-05-0

Isochroman

Learn More
N/A Structure

119367-93-0

N/A

~%

Isochroman Structure

493-05-0

Isochroman

Learn More
2-(2-(Benzyloxy)ethyl)benzoic acid Structure

119367-92-9

2-(2-(Benzyloxy...

~%

Isochroman Structure

493-05-0

Isochroman

Learn More
Benzenemethanol, 2-(2-methoxyethyl) Structure

119367-72-5

Benzenemethanol...

~%

Isochroman Structure

493-05-0

Isochroman

Learn More
N/A Structure

119367-73-6

N/A

~%

Isochroman Structure

493-05-0

Isochroman

Learn More
N/A Structure

119367-74-7

N/A

~%

Isochroman Structure

493-05-0

Isochroman

Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

earthy indane Structure

1006-27-5

earthy indane

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

Detail Learn More
2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

119367-60-1

2-(Methoxymethy...

~%

Phthalane Structure

496-14-0

Phthalane

Isochroman Structure

493-05-0

Isochroman

α-methoxy-α,α'-dihydrobenzocyclobutene Structure

36101-23-2

α-methoxy-α,α'-...

Detail Learn More
N/A Structure

119367-74-7

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1-methyl-3,4-dihydro-1H-isochromene Structure

26164-06-7

1-methyl-3,4-di...

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

Detail Learn More
N/A Structure

119367-74-7

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

Detail Learn More
N/A Structure

119367-74-7

N/A

~%

Isochroman Structure

493-05-0

Isochroman

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

1-(2-Methoxyethyl)-2-(methoxymethyl)benzene Structure

15018-15-2

1-(2-Methoxyeth...

Detail Learn More
N/A Structure

119367-74-7

N/A

~%

Isochroman Structure

493-05-0

Isochroman

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

1-(2-Methoxyethyl)-2-(methoxymethyl)benzene Structure

15018-15-2

1-(2-Methoxyeth...

Detail Learn More
2-(2-(Benzyloxy)ethyl)benzaldehyde tosylhydrazone Structure

119367-95-2

2-(2-(Benzyloxy...

~%

Isochroman Structure

493-05-0

Isochroman

1-Benzyl-3,4-dihydro-1H-2-benzopyran Structure

23107-95-1

1-Benzyl-3,4-di...

2-(Benzyloxy)indan Structure

78370-74-8

2-(Benzyloxy)indan

Detail Learn More
2-(2-(Benzyloxy)ethyl)benzaldehyde tosylhydrazone Structure

119367-95-2

2-(2-(Benzyloxy...

~%

Isochroman Structure

493-05-0

Isochroman

N/A Structure

119367-62-3

N/A

2-(Benzyloxy)indan Structure

78370-74-8

2-(Benzyloxy)indan

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

N/A Structure

119367-76-9

N/A

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

1-(2-Methoxyethyl)-2-(methoxymethyl)benzene Structure

15018-15-2

1-(2-Methoxyeth...

Detail Learn More
Methanol Structure

67-56-1

Methanol

N/A Structure

119367-74-7

N/A

~%

Isochroman Structure

493-05-0

Isochroman

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

Detail Learn More
2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

119367-60-1

2-(Methoxymethy...

tert-Butanol Structure

75-65-0

tert-Butanol

~%

Phthalane Structure

496-14-0

Phthalane

Isochroman Structure

493-05-0

Isochroman

Detail Learn More
sodium 2-(2-(methoxymethyl)benzylidene)-1-tosylhydrazin-1-ide Structure

119391-23-0

sodium 2-(2-(me...

~%

Isochroman Structure

493-05-0

Isochroman

2-(2-Methylphenyl)oxirane Structure

2783-26-8

2-(2-Methylphen...

2-Ethylbenzaldehyde Structure

22927-13-5

2-Ethylbenzaldehyde

Detail Learn More
N/A Structure

119367-74-7

N/A

~%

Isochroman Structure

493-05-0

Isochroman

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

N/A Structure

119367-76-9

N/A

Detail Learn More
diglyme Structure

111-96-6

diglyme

sodium 2-(2-(methoxymethyl)benzylidene)-1-tosylhydrazin-1-ide Structure

119391-23-0

sodium 2-(2-(me...

~%

Phthalane Structure

496-14-0

Phthalane

Isochroman Structure

493-05-0

Isochroman

Detail Learn More
2-(2-(Benzyloxy)ethyl)benzaldehyde tosylhydrazone Structure

119367-95-2

2-(2-(Benzyloxy...

~%

Isochroman Structure

493-05-0

Isochroman

1-Benzyl-3,4-dihydro-1H-2-benzopyran Structure

23107-95-1

1-Benzyl-3,4-di...

N/A Structure

119367-63-4

N/A

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1-methyl-3,4-dihydro-1H-isochromene Structure

26164-06-7

1-methyl-3,4-di...

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

Detail Learn More
sodium 2-(2-(methoxymethyl)benzylidene)-1-tosylhydrazin-1-ide Structure

119391-23-0

sodium 2-(2-(me...

~%

Phthalane Structure

496-14-0

Phthalane

Isochroman Structure

493-05-0

Isochroman

α-methoxy-α,α'-dihydrobenzocyclobutene Structure

36101-23-2

α-methoxy-α,α'-...

Detail Learn More
Methanol Structure

67-56-1

Methanol

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

119367-60-1

2-(Methoxymethy...

~%

Phthalane Structure

496-14-0

Phthalane

Isochroman Structure

493-05-0

Isochroman

Detail Learn More
Ethanol Structure

64-17-5

Ethanol

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

119367-60-1

2-(Methoxymethy...

~%

Phthalane Structure

496-14-0

Phthalane

Isochroman Structure

493-05-0

Isochroman

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

earthy indane Structure

1006-27-5

earthy indane

Detail Learn More
2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

119367-60-1

2-(Methoxymethy...

tert-Butanol Structure

75-65-0

tert-Butanol

~%

Phthalane Structure

496-14-0

Phthalane

Isochroman Structure

493-05-0

Isochroman

Detail Learn More
(Z)-3-benzylidenephthalide Structure

4767-56-0

(Z)-3-benzylide...

~91%

3-benzylphthalide Structure

7011-98-5

3-benzylphthalide

Learn More
N'-(2-((benzyloxy)methyl)benzylidene)-4-methylbenzenesulfonohydrazide Structure

119367-66-7

N'-(2-((benzylo...

~%

Phthalane Structure

496-14-0

Phthalane

N/A Structure

119367-68-9

N/A

N/A Structure

119367-71-4

N/A

Detail Learn More
1-(1,3-Dioxolan-2-yl)benzaldehyde tosylhydrazone Structure

119367-79-2

1-(1,3-Dioxolan...

~%

Spiro[bicyclo[4.2.0]octa-1,3,5-triene-7,2'-[1,3]dioxolane] (en) Structure

14458-33-4

Spiro[bicyclo[4...

N/A Structure

119368-01-3

N/A

N/A Structure

119367-83-8

N/A

Detail Learn More
sodium 2-(2-(1,3-dioxolan-2-yl)benzylidene)-1-tosylhydrazin-1-ide Structure

119391-27-4

sodium 2-(2-(1,...

~%

Spiro[bicyclo[4.2.0]octa-1,3,5-triene-7,2'-[1,3]dioxolane] (en) Structure

14458-33-4

Spiro[bicyclo[4...

N/A Structure

119368-01-3

N/A

N/A Structure

119367-82-7

N/A

Detail Learn More
N/A Structure

119367-74-7

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

1-methyl-3,4-dihydro-1H-isochromene Structure

26164-06-7

1-methyl-3,4-di...

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

earthy indane Structure

1006-27-5

earthy indane

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

N/A Structure

119367-76-9

N/A

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

earthy indane Structure

1006-27-5

earthy indane

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1-methyl-3,4-dihydro-1H-isochromene Structure

26164-06-7

1-methyl-3,4-di...

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

Detail Learn More
N/A Structure

119367-74-7

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1-methyl-3,4-dihydro-1H-isochromene Structure

26164-06-7

1-methyl-3,4-di...

indan-2-yl methyl ether Structure

81887-53-8

indan-2-yl meth...

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

1-methyl-3,4-dihydro-1H-isochromene Structure

26164-06-7

1-methyl-3,4-di...

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

earthy indane Structure

1006-27-5

earthy indane

Detail Learn More
N/A Structure

119391-26-3

N/A

~%

Isochroman Structure

493-05-0

Isochroman

1-methyl-3,4-dihydro-1H-isochromene Structure

26164-06-7

1-methyl-3,4-di...

1,2,4,5-Tetrahydrobenzo[d]oxepine Structure

5368-66-1

1,2,4,5-Tetrahy...

Detail Learn More

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