e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

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 ...

Methanol Structure

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

2-(Methoxymethy...

~%

Phthalane Structure

N/A Structure

Detail

diglyme Structure

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

sodium 2-(2-(me...

~%

Phthalane Structure

Isochroman Structure

Detail

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

sodium 2-(2-(me...

~%

Phthalane Structure

Isochroman Structure

α-methoxy-α,α'-dihydrobenzocyclobutene Structure

α-methoxy-α,α'-...

Detail

Methanol Structure

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

2-(Methoxymethy...

~%

Phthalane Structure

Isochroman Structure

Detail

Phthalide Structure

~%

Benzyl methyl ether Structure

Benzyl methyl ether

2-((Benzyloxy)methyl)benzyl alcohol Structure

2-((Benzyloxy)m...

~%

Benzyl methyl ether Structure

Benzyl methyl ether

2-(Phenylmethoxymethyl)benzaldehyde Structure

2-(Phenylmethox...

~%

Benzyl methyl ether Structure

Benzyl methyl ether

2-[(Benzyloxy)methyl]benzoic acid Structure

2-[(Benzyloxy)m...

~%

Benzyl methyl ether Structure

Benzyl methyl ether

N/A Structure

~%

Benzyl methyl ether Structure

Benzyl methyl ether

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

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

~%

Benzyl methyl ether Structure

Benzyl methyl ether

Phthalane Structure

N/A Structure

Detail

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

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

~%

Benzyl methyl ether Structure

Benzyl methyl ether

Phthalane Structure

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

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

Detail

Methanol Structure

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

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

~%

Benzyl methyl ether Structure

Benzyl methyl ether

Phthalane Structure

Detail

Methanol Structure

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

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

~%

Benzyl methyl ether Structure

Benzyl methyl ether

Phthalane Structure

Detail

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

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

~%

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

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

2-PHENETHYLBENZALDEHYDE Structure

2-PHENETHYLBENZ...

N/A Structure

Detail

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

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

~%

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

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

2-PHENETHYLBENZALDEHYDE Structure

2-PHENETHYLBENZ...

N/A Structure

Detail

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

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

~%

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

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

2-PHENETHYLBENZALDEHYDE Structure

2-PHENETHYLBENZ...

Bibenzyl Structure

Detail

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

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

~%

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

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

2-PHENETHYLBENZALDEHYDE Structure

2-PHENETHYLBENZ...

Bibenzyl Structure

Detail

Methanol Structure

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

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

~%

Benzyl methyl ether Structure

Benzyl methyl ether

Phthalane Structure

Detail

Benzenemethanol, 2-(methoxymethyl)- (9CI) Structure

Benzenemethanol...

~75%

2-(methoxymethyl)benzaldehyde Structure

2-(methoxymethy...

Isochroman-1-one Structure

Isochroman-1-one

~%

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

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

N/A Structure

~%

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

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

N/A Structure

~%

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

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

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

2-(2-(Benzyloxy...

~%

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

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

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

2-(2-(Benzyloxy...

~%

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

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

Benzenemethanol, 2-(2-methoxyethyl)- Structure

Benzenemethanol...

~%

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

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

N/A Structure

~%

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

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

N/A Structure

~%

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

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

N/A Structure

~%

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

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

N/A Structure

~%

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

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

N/A Structure

~8%

Isochroman Structure

N/A Structure

N/A Structure

~%

Isochroman Structure

N/A Structure

~%

Isochroman Structure

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

2-(2-(Benzyloxy...

~%

Isochroman Structure

Benzenemethanol, 2-(2-methoxyethyl)- Structure

Benzenemethanol...

~%

Isochroman Structure

N/A Structure

~%

Isochroman Structure

N/A Structure

~%

Isochroman Structure

N/A Structure

~%

Isochroman Structure

N/A Structure

~%

Isochroman Structure

earthy indane Structure

indan-2-yl methyl ether Structure

indan-2-yl meth...

Detail

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

2-(Methoxymethy...

~%

Phthalane Structure

Isochroman Structure

α-methoxy-α,α'-dihydrobenzocyclobutene Structure

α-methoxy-α,α'-...

Detail

N/A Structure

~%

Isochroman Structure

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

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

indan-2-yl methyl ether Structure

indan-2-yl meth...

Detail

N/A Structure

~%

Isochroman Structure

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

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

indan-2-yl methyl ether Structure

indan-2-yl meth...

Detail

N/A Structure

~%

Isochroman Structure

indan-2-yl methyl ether Structure

indan-2-yl meth...

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

1-(2-Methoxyeth...

Detail

N/A Structure

~%

Isochroman Structure

indan-2-yl methyl ether Structure

indan-2-yl meth...

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

1-(2-Methoxyeth...

Detail

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

2-(2-(Benzyloxy...

~%

Isochroman Structure

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

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

2-(Benzyloxy)indan Structure

2-(Benzyloxy)indan

Detail

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

2-(2-(Benzyloxy...

~%

Isochroman Structure

N/A Structure

2-(Benzyloxy)indan Structure

2-(Benzyloxy)indan

Detail

N/A Structure

~%

Isochroman Structure

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

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

indan-2-yl methyl ether Structure

indan-2-yl meth...

Detail

N/A Structure

~%

Isochroman Structure

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

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

N/A Structure

Detail

N/A Structure

~%

Isochroman Structure

indan-2-yl methyl ether Structure

indan-2-yl meth...

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

1-(2-Methoxyeth...

Detail

Methanol Structure

N/A Structure

~%

Isochroman Structure

indan-2-yl methyl ether Structure

indan-2-yl meth...

Detail

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

2-(Methoxymethy...

tert-Butanol Structure

~%

Phthalane Structure

Isochroman Structure

Detail

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

sodium 2-(2-(me...

~%

Isochroman Structure

2-(2-Methylphenyl)oxirane Structure

2-(2-Methylphen...

2-Ethylbenzaldehyde Structure

2-Ethylbenzaldehyde

Detail

N/A Structure

~%

Isochroman Structure

indan-2-yl methyl ether Structure

indan-2-yl meth...

N/A Structure

Detail

diglyme Structure

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

sodium 2-(2-(me...

~%

Phthalane Structure

Isochroman Structure

Detail

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

2-(2-(Benzyloxy...

~%

Isochroman Structure

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

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

N/A Structure

Detail

N/A Structure

~%

Isochroman Structure

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

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

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

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

Detail

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

sodium 2-(2-(me...

~%

Phthalane Structure

Isochroman Structure

α-methoxy-α,α'-dihydrobenzocyclobutene Structure

α-methoxy-α,α'-...

Detail

Methanol Structure

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

2-(Methoxymethy...

~%

Phthalane Structure

Isochroman Structure

Detail

Ethanol Structure

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

2-(Methoxymethy...

~%

Phthalane Structure

Isochroman Structure

Detail

N/A Structure

~%

Isochroman Structure

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

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

earthy indane Structure

Detail

2-(Methoxymethyl)benzaldehyde tosylhydrazone Structure

2-(Methoxymethy...

tert-Butanol Structure

~%

Phthalane Structure

Isochroman Structure

Detail

(Z)-3-benzylidenephthalide Structure

(Z)-3-benzylide...

~91%

3-benzylphthalide Structure

3-benzylphthalide

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

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

~%

Phthalane Structure

N/A Structure

N/A Structure

Detail

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

1-(1,3-Dioxolan...

~%

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

Spiro[bicyclo[4...

N/A Structure

N/A Structure

Detail

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

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

~%

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

Spiro[bicyclo[4...

N/A Structure

N/A Structure

Detail

N/A Structure

~%

Isochroman Structure

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

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

indan-2-yl methyl ether Structure

indan-2-yl meth...

Detail

N/A Structure

~%

Isochroman Structure

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

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

indan-2-yl methyl ether Structure

indan-2-yl meth...

Detail

N/A Structure

~%

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

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

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

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

earthy indane Structure

Detail

N/A Structure

~%

Isochroman Structure

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

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

N/A Structure

Detail

N/A Structure

~%

Isochroman Structure

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

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

earthy indane Structure

Detail

N/A Structure

~%

Isochroman Structure

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

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

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

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

Detail

N/A Structure

~%

Isochroman Structure

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

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

indan-2-yl methyl ether Structure

indan-2-yl meth...

Detail

N/A Structure

~%

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

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

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

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

earthy indane Structure

Detail

N/A Structure

~%

Isochroman Structure

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

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

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

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

Detail