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

The Journal of Organic Chemistry

Carbenes and the oxygen-hydrogen bond: hydroxyalkyl-substituted arylcarbenes

W Kirmse, K Kund

Index: Kirmse, Wolfgang; Kund, Klaus Journal of Organic Chemistry, 1990 , vol. 55, # 8 p. 2325 - 2332

Full Text: HTML

Citation Number: 25

Abstract

[2-(H ydroxymethyl) phenyl] carbene (4),[2-(hydroxymethy1) phen yl] phenylcarbene (19), and [2-(2-hydroxyethy1) phenyllcarbene (30) have been generated by photolysis of tosylhydrazone or diazo precursors in protic solvents. These carbenes give cyclic ethers (7, 18, 33) competitively with insertion into 0-H bonds of the solvent. For comparison, the analogous benzyl cations (9, 17, 31) have been generated by solvolysis or dediazoniation ...

Isochroman-1-one Structure

Isochroman-1-one

~%

2-[2-(hydroxymethyl)phenyl]ethanol Structure

2-[2-(hydroxyme...

3,4-dihydro-1H-isochromen-1-ol Structure

3,4-dihydro-1H-...

N/A Structure

~%

Isochroman Structure

2-[2-(hydroxymethyl)phenyl]ethanol Structure

2-[2-(hydroxyme...

3,4-dihydro-1H-isochromen-1-ol Structure

3,4-dihydro-1H-...

~%

2-[2-(hydroxymethyl)phenyl]ethanol Structure

2-[2-(hydroxyme...

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

2-[2-(hydroxymethyl)phenyl]ethanol Structure

2-[2-(hydroxyme...

2-(2-hydroxyethyl)benzylamine hydrochloride Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-[2-(hydroxymethyl)phenyl]ethanol Structure

2-[2-(hydroxyme...

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

2-(2-Methylphenyl)ethanol Structure

2-(2-Methylphen...

Detail

N/A Structure

~%

2-[2-(hydroxymethyl)phenyl]ethanol Structure

2-[2-(hydroxyme...

Isochroman-1-one Structure

Isochroman-1-one

~%

2-[2-(hydroxymethyl)phenyl]ethanol Structure

2-[2-(hydroxyme...

3,4-dihydro-1H-isochromen-1-ol Structure

3,4-dihydro-1H-...

Sodium Methylate Structure

Sodium Methylate

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

Detail

N/A Structure

~%

Isochroman Structure

2-Indanol Structure

2-(2-Methylphenyl)ethanol Structure

2-(2-Methylphen...

Detail

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

2-(2-Methylphenyl)ethanol Structure

2-(2-Methylphen...

Detail

Sodium Methylate Structure

Sodium Methylate

N/A Structure

~%

Isochroman Structure

2-Indanol Structure

Detail

Sodium Methylate Structure

Sodium Methylate

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

Detail

Sodium ethoxide Structure

Sodium ethoxide

N/A Structure

~%

Isochroman Structure

2-Indanol Structure

Detail

Sodium ethoxide Structure

Sodium ethoxide

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

Detail

Sodium 2,2,2-trifluoroethanolate Structure

Sodium 2,2,2-tr...

N/A Structure

~%

Isochroman Structure

2-Indanol Structure

Detail

Sodium 2,2,2-trifluoroethanolate Structure

Sodium 2,2,2-tr...

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

Detail

3,4-dihydro-1H-isochromen-1-ol Structure

3,4-dihydro-1H-...

~%

2-Indanol Structure

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

2-Indanol Structure

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

2-(2-Methylphenyl)ethanol Structure

2-(2-Methylphen...

Detail

Sodium Methylate Structure

Sodium Methylate

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

Detail

Isochroman-1-one Structure

Isochroman-1-one

~%

Isochroman Structure

N/A Structure

~%

Isochroman Structure

2-[2-(hydroxymethyl)phenyl]ethanol Structure

2-[2-(hydroxyme...

3,4-dihydro-1H-isochromen-1-ol Structure

3,4-dihydro-1H-...

~%

Isochroman Structure

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

Methanol Structure

N/A Structure

~%

Isochroman Structure

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

Benzeneethanol,...

Ethanol Structure

N/A Structure

~%

Isochroman Structure

2-ethoxymethyl-phenethyl alcohol Structure

2-ethoxymethyl-...

N/A Structure

~%

Isochroman Structure

2-Indanol Structure

2-(2-Methylphenyl)ethanol Structure

2-(2-Methylphen...

Detail

N/A Structure

tert-Butanol Structure

~%

Isochroman Structure

N/A Structure

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

2-(2-Methylphenyl)ethanol Structure

2-(2-Methylphen...

Detail

Sodium Methylate Structure

Sodium Methylate

N/A Structure

~%

Isochroman Structure

2-Indanol Structure

Detail

Sodium Methylate Structure

Sodium Methylate

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

Detail

Sodium ethoxide Structure

Sodium ethoxide

N/A Structure

~%

Isochroman Structure

2-Indanol Structure

Detail

Sodium ethoxide Structure

Sodium ethoxide

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

Detail

Sodium 2,2,2-trifluoroethanolate Structure

Sodium 2,2,2-tr...

N/A Structure

~%

Isochroman Structure

2-Indanol Structure

Detail

Sodium 2,2,2-trifluoroethanolate Structure

Sodium 2,2,2-tr...

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

Detail

N/A Structure

~%

Isochroman Structure

2-(2-hydroxyethyl)benzylamine hydrochloride Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-[2-(hydroxymethyl)phenyl]ethanol Structure

2-[2-(hydroxyme...

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

2-(2-Methylphenyl)ethanol Structure

2-(2-Methylphen...

Detail

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

N/A Structure

~%

Isochroman Structure

N/A Structure

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

N/A Structure

Sodium Methylate Structure

Sodium Methylate

2-(2-hydroxyethyl)benzaldehyde tosylhydrazone Structure

2-(2-hydroxyeth...

~%

Isochroman Structure

2-Indanol Structure

Detail

4-Methylbenzenesulfonhydrazide Structure

4-Methylbenzene...

~%

[2-(aminomethyl)phenyl]methanol,hydrochloride Structure

[2-(aminomethyl...

Isochroman-1-one Structure

Isochroman-1-one

~%

2-Indanol Structure

Sodium Methylate Structure

Sodium Methylate

2-(hydroxymethyl)benzaldehyde tosylhydrazone Structure

2-(hydroxymethy...

~%

Phthalane Structure

Phthalide Structure

Detail

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Mechanism of the reaction between benzylmagnesium chloride a...

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The synthesis of aminobenzazepinones as anti-phenylalanine d...

[Warshawsky, Alan M.; Flynn, Gary A.; Koehl, Jack R.; Mehdi, Shujaath; Vaz, Roy J. Bioorganic and Medicinal Chemistry Letters, 1996 , vol. 6, # 8 p. 957 - 962]

Activated iodosylbenzene monomer as an ozone equivalent: oxi...

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Diastereo-and enantioselective synthesis of 1, 2-diols by va...

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