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

3, 3, 9, 9-Tetramethyl-1, 5, 7, 11-tetraoxaspiro [5.5] undecane as a reagent for protection of carbonyl compounds

…, M Bakavoli, A Shiri, H Eshghi, S Saberi

Index: Rahimizadeh, Mohammad; Bakavoli, Mehdi; Shiri, Ali; Eshghi, Hossein; Saberi, Sattar Journal of Chemical Research, 2008 , # 12 p. 704 - 706

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Citation Number: 4

Abstract

The protection of carbonyl groups as acetals or ketals and their subsequent regenerations is an important strategy in a multi-stage organic synthesis.l Numerous attempts to improve the efficiency of this process have been investigated and a number of strategies, such as the use of protic acids, Lewis acids, solid acids and ionic liquids as the catalyst, with 1,2- diols, 1,3-diols, 1,2-dithiols, 1,3-dithiols and orthoesters as the protecting reagents,2 have been reported. ...

spiroorthocarbonate Structure

spiroorthocarbonate

3-Nitrobenzaldehyde Structure

3-Nitrobenzaldehyde

~94%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

1,3-Dioxane,5,5-dimethyl-2-(3-nitrophenyl)- Structure

1,3-Dioxane,5,5...

spiroorthocarbonate Structure

spiroorthocarbonate

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

~97%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxane Structure

2-(4-chlorophen...

spiroorthocarbonate Structure

spiroorthocarbonate

naphthal Structure

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

N/A Structure

spiroorthocarbonate Structure

spiroorthocarbonate

2,4-dimethyl-3-pentanone Structure

2,4-dimethyl-3-...

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

2,2-diisopropyl-5,5-dimethyl-1,3-dioxane Structure

2,2-diisopropyl...

spiroorthocarbonate Structure

spiroorthocarbonate

Benzaldehyde Structure

~92%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

1,3-Dioxane,5,5-dimethyl-2-phenyl- Structure

1,3-Dioxane,5,5...

spiroorthocarbonate Structure

spiroorthocarbonate

Acetophenone Structure

~88%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

1,3-Dioxane,2,5,5-trimethyl-2-phenyl- Structure

1,3-Dioxane,2,5...

spiroorthocarbonate Structure

spiroorthocarbonate

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~81%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

1-[(3-bromophenyl)methyl]-3-(4-ethoxyphenyl)-1-(oxolan-2-ylmethyl)thiourea Structure

1-[(3-bromophen...

spiroorthocarbonate Structure

spiroorthocarbonate

Cyclohexanone Structure

~92%

1,5-Dioxaspiro[5.5]undecane,3,3-dimethyl- Structure

1,5-Dioxaspiro[...

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

spiroorthocarbonate Structure

spiroorthocarbonate

p-Tolualdehyde Structure

~88%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

1,3-Dioxane,5,5-dimethyl-2-(4-methylphenyl)- Structure

1,3-Dioxane,5,5...

spiroorthocarbonate Structure

spiroorthocarbonate

Cyclopentanone Structure

~87%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

6,10-Dioxaspiro[4.5]decane,8,8-dimethyl- Structure

6,10-Dioxaspiro...

spiroorthocarbonate Structure

spiroorthocarbonate

Cyclohexanone Structure

~0%

1,5-Dioxaspiro[5.5]undecane,3,3-dimethyl- Structure

1,5-Dioxaspiro[...

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

spiroorthocarbonate Structure

spiroorthocarbonate

p-Tolualdehyde Structure

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

1,3-Dioxane,5,5-dimethyl-2-(4-methylphenyl)- Structure

1,3-Dioxane,5,5...

spiroorthocarbonate Structure

spiroorthocarbonate

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxane Structure

2-(4-chlorophen...

spiroorthocarbonate Structure

spiroorthocarbonate

3-Nitrobenzaldehyde Structure

3-Nitrobenzaldehyde

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

1,3-Dioxane,5,5-dimethyl-2-(3-nitrophenyl)- Structure

1,3-Dioxane,5,5...

spiroorthocarbonate Structure

spiroorthocarbonate

4-Nitrobenzaldehyde Structure

4-Nitrobenzaldehyde

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

(4'-nitrophenyl)-2,2-dimethyl-1,3-dioxolane Structure

(4'-nitrophenyl...

spiroorthocarbonate Structure

spiroorthocarbonate

Benzaldehyde Structure

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

1,3-Dioxane,5,5-dimethyl-2-phenyl- Structure

1,3-Dioxane,5,5...

spiroorthocarbonate Structure

spiroorthocarbonate

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

2-(4-bromophenyl)-5,5-dimethyl-1,3-dioxane Structure

2-(4-bromopheny...

spiroorthocarbonate Structure

spiroorthocarbonate

Cyclopentanone Structure

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

6,10-Dioxaspiro[4.5]decane,8,8-dimethyl- Structure

6,10-Dioxaspiro...

spiroorthocarbonate Structure

spiroorthocarbonate

Acetophenone Structure

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

1,3-Dioxane,2,5,5-trimethyl-2-phenyl- Structure

1,3-Dioxane,2,5...

Valeraldehyde Structure

spiroorthocarbonate Structure

spiroorthocarbonate

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

2-n-butyl-5,5-dimethyl-1,3-dioxane Structure

2-n-butyl-5,5-d...

spiroorthocarbonate Structure

spiroorthocarbonate

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

1-[(3-bromophenyl)methyl]-3-(4-ethoxyphenyl)-1-(oxolan-2-ylmethyl)thiourea Structure

1-[(3-bromophen...

spiroorthocarbonate Structure

spiroorthocarbonate

m-Anisaldehyde Structure

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

N/A Structure

spiroorthocarbonate Structure

spiroorthocarbonate

o-Anisaldehyde Structure

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

2-(2-methoxyphenyl)-5,5-dimethyl-1,3-dioxane Structure

2-(2-methoxyphe...

spiroorthocarbonate Structure

spiroorthocarbonate

2-Bromoacetophenone Structure

2-Bromoacetophenone

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

2-(Bromomethyl)-5,5-dimethyl-2-phenyl-1,3-dioxane Structure

2-(Bromomethyl)...

Benzophenone Structure

spiroorthocarbonate Structure

spiroorthocarbonate

~0%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

5,5-dimethyl-2,2-diphenyl-1,3-dioxane Structure

5,5-dimethyl-2,...

spiroorthocarbonate Structure

spiroorthocarbonate

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~97%

1,3-Dioxan-2-one,5,5-dimethyl- Structure

1,3-Dioxan-2-on...

2-(4-bromophenyl)-5,5-dimethyl-1,3-dioxane Structure

2-(4-bromopheny...

Synthesis of N-arylpyridinium salts bearing a nitrone spin t...

[Robertson, Linsey; Hartley, Richard C. Tetrahedron, 2009 , vol. 65, # 27 p. 5284 - 5292]