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

Hydroxyalkylation with. alpha.-hydroperoxydiazenes. Alcohols from olefins and carbonyl compounds from enol ethers

EY Osei-Twum, D McCallion, AS Nazran…

Index: Osei-Twum, Emmanuel Y.; McCallion, Doug; Nazran, Avtar S.; Panicucci, Rick; Risbood, Prabhakar A.; Warkentin, John Journal of Organic Chemistry, 1984 , vol. 49, # 2 p. 336 - 342

Full Text: HTML

Citation Number: 13

Abstract

Alkyl (1-hydroperoxy-1-methylethy1) diazenes 2a-f [(CH,), C (OOH) N= NR: a, R= CHzCF3; b, R= CHzCH2CN; c, R= CHzCH (CH3) CN; d, R= CHzCH20CH3; e, R= CH2CH20C6H5; f, R= CH2CHzCH20C6H5)] were prepared in solution by autoxidation of the corresponding hydrazones of acetone. Thermolysis of the diazenes at 50-80" C in alkenes leads to alcohols. For example, 2b decomposes in 1, l-diphenylethene to afford 5-hydroxy-5, 5- ...

3-hydrazinyl-2-methylpropanenitrile Structure

3-hydrazinyl-2-...

Acetone Structure

~%

2-methyl-3-(2-propan-2-ylidenehydrazinyl)propanenitrile Structure

2-methyl-3-(2-p...

1,1,1-trifluoro-2-((1-methylethylidene)hydrazino)ethane Structure

1,1,1-trifluoro...

~%

2-hydroperoxypropan-2-yl(2,2,2-trifluoroethyl)diazene Structure

2-hydroperoxypr...

3-(2-hydroperoxypropan-2-yldiazenyl)-2-methylpropanenitrile Structure

3-(2-hydroperox...

Ethoxyethene Structure

~66%

2-methyl-5-oxopentanenitrile Structure

2-methyl-5-oxop...

3-[(1-methylethylidene)hydrazino]propanenitrile Structure

3-[(1-methyleth...

~%

3-(2-hydroperoxypropan-2-yldiazenyl)propanenitrile Structure

3-(2-hydroperox...

2-methyl-3-(2-propan-2-ylidenehydrazinyl)propanenitrile Structure

2-methyl-3-(2-p...

~%

3-(2-hydroperoxypropan-2-yldiazenyl)-2-methylpropanenitrile Structure

3-(2-hydroperox...

β-Bromophenetole Structure

β-Bromophenetole

~%

2-hydroperoxypropan-2-yl(2-phenoxyethyl)diazene Structure

2-hydroperoxypr...

2-methyoxypropene Structure

2-methyoxypropene

3-(2-hydroperoxypropan-2-yldiazenyl)propanenitrile Structure

3-(2-hydroperox...

~62%

5-Ketohexanenitrile Structure

5-Ketohexanenitrile

1-phenoxy-3-((1-methylethylidene)hydrazino)propane Structure

1-phenoxy-3-((1...

~%

2-hydroperoxypropan-2-yl(3-phenoxypropyl)diazene Structure

2-hydroperoxypr...

1-(3-NITRO-PHENYL)-ETHYLAMINE Structure

1-(3-NITRO-PHEN...

~%

2-hydroperoxypropan-2-yl(3-phenoxypropyl)diazene Structure

2-hydroperoxypr...

(3-Bromopropoxy)benzene Structure

(3-Bromopropoxy...

~%

2-hydroperoxypropan-2-yl(3-phenoxypropyl)diazene Structure

2-hydroperoxypr...

3-(2-hydroperoxypropan-2-yldiazenyl)propanenitrile Structure

3-(2-hydroperox...

Ethoxyethene Structure

~68%

5-oxopentanenitrile Structure

5-oxopentanenitrile

2-hydroperoxypropan-2-yl(2,2,2-trifluoroethyl)diazene Structure

2-hydroperoxypr...

Ethoxyethene Structure

~69%

4,4,4-Trifluorobutanal Structure

4,4,4-Trifluoro...

2-methyoxypropene Structure

2-methyoxypropene

2-hydroperoxypropan-2-yl(2-phenoxyethyl)diazene Structure

2-hydroperoxypr...

~74%

5-phenoxypentan-2-one Structure

5-phenoxypentan...

β-Bromophenetole Structure

β-Bromophenetole

~%

5-phenoxypentan-2-one Structure

5-phenoxypentan...

(3-Bromopropoxy)benzene Structure

(3-Bromopropoxy...

~74%

1-(3-NITRO-PHENYL)-ETHYLAMINE Structure

1-(3-NITRO-PHEN...

(3-Bromopropoxy)benzene Structure

(3-Bromopropoxy...

~%

6-PHENOXY-HEXAN-2-ONE Structure

6-PHENOXY-HEXAN...

2-methyoxypropene Structure

2-methyoxypropene

2-hydroperoxypropan-2-yl(3-phenoxypropyl)diazene Structure

2-hydroperoxypr...

~63%

6-PHENOXY-HEXAN-2-ONE Structure

6-PHENOXY-HEXAN...

1-(3-NITRO-PHENYL)-ETHYLAMINE Structure

1-(3-NITRO-PHEN...

~%

6-PHENOXY-HEXAN-2-ONE Structure

6-PHENOXY-HEXAN...

1-phenoxy-3-((1-methylethylidene)hydrazino)propane Structure

1-phenoxy-3-((1...

~%

6-PHENOXY-HEXAN-2-ONE Structure

6-PHENOXY-HEXAN...

2-hydroperoxypropan-2-yl(3-phenoxypropyl)diazene Structure

2-hydroperoxypr...

Ethoxyethene Structure

~61%

5-phenoxypentanal Structure

5-phenoxypentanal

1-(3-NITRO-PHENYL)-ETHYLAMINE Structure

1-(3-NITRO-PHEN...

~%

5-phenoxypentanal Structure

5-phenoxypentanal

1-phenoxy-3-((1-methylethylidene)hydrazino)propane Structure

1-phenoxy-3-((1...

~%

5-phenoxypentanal Structure

5-phenoxypentanal

(3-Bromopropoxy)benzene Structure

(3-Bromopropoxy...

~%

5-phenoxypentanal Structure

5-phenoxypentanal

2-hydroperoxypropan-2-yl(2-phenoxyethyl)diazene Structure

2-hydroperoxypr...

Ethoxyethene Structure

~50%

CHROMAN Structure

Phenoxyethanol Structure

Detail

2-hydroperoxypropan-2-yl(2-phenoxyethyl)diazene Structure

2-hydroperoxypr...

Ethoxyethene Structure

~0%

CHROMAN Structure

Phenoxyethanol Structure

Detail

2-hydroperoxypropan-2-yl(2-phenoxyethyl)diazene Structure

2-hydroperoxypr...

Ethoxyethene Structure

~65%

4-phenoxybutanal Structure

4-phenoxybutanal

β-Bromophenetole Structure

β-Bromophenetole

~%

4-phenoxybutanal Structure

4-phenoxybutanal

2-hydroperoxypropan-2-yl(2-phenoxyethyl)diazene Structure

2-hydroperoxypr...

Ethoxyethene Structure

~1%

CHROMAN Structure

Phenoxyethanol Structure

Detail

2-Methoxyethyl 4-methylbenzenesulfonate Structure

2-Methoxyethyl ...

~%

(2-Methoxyethyl)hydrazine Structure

(2-Methoxyethyl...

Acrylonitrile Structure

~94%

2-cyanoethylhydrazine Structure

2-cyanoethylhyd...