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

A Homologous Series of O??and N??Functionalized 2, 2??Difluoro1, 3??benzodioxoles: an Exercise in Organometallic Methodology

…, J Gorecka, E Castagnetti

Index: Schlosser, Manfred; Gorecka, Joanna; Castagnetti, Eva European Journal of Organic Chemistry, 2003 , # 3 p. 452 - 462

Full Text: HTML

Citation Number: 10

Abstract

Abstract The conversion of 2, 2-difluoro-1, 3-benzodioxole, an exceptionally acidic arene, via a 4-lithiated intermediate into more than three dozen new derivatives was conceived as a case study. The lithiated species was trapped by C 0-electrophiles (4-toluenesulfonyl azide, fluorodimethoxyborane, iodine), C 1-electrophiles (carbon dioxide, N, N- dimethylformamide, formaldehyde, dimethyl sulfate), C 2-electrophiles (oxalic acid ...

2,2-Difluoro-1,3-benzodioxole Structure

2,2-Difluoro-1,...

~71%

4-Bromo-2,2-difluoro-1,3-benzodioxole Structure

4-Bromo-2,2-dif...

2,2-Difluoro-1,3-benzodioxole Structure

2,2-Difluoro-1,...

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~88%

2,2-Difluoro-1,3-benzodioxole-4-carbaldehyde Structure

2,2-Difluoro-1,...

2,2-Difluoro-1,3-benzodioxole Structure

2,2-Difluoro-1,...

Methyl chloroformate Structure

Methyl chloroformate

~81%

methyl 2,2-difluoro-1,3-benzodioxole-4-carboxylate Structure

methyl 2,2-difl...

Methanol Structure

2,2-Difluoro-1,3-benzodioxole-4-carboxylic acid Structure

2,2-Difluoro-1,...

~88%

methyl 2,2-difluoro-1,3-benzodioxole-4-carboxylate Structure

methyl 2,2-difl...

2,2-Difluoro-1,3-benzodioxole Structure

2,2-Difluoro-1,...

~99%

2,2-difluoro-4-iodo-1,3-benzodioxole Structure

2,2-difluoro-4-...

METHYLLITHIUM Structure

2,2-Difluoro-1,3-benzodioxole-4-carboxylic acid Structure

2,2-Difluoro-1,...

~68%

1-(2,2-difluoro-1,3-benzodioxol-4-yl)ethanone Structure

1-(2,2-difluoro...

2,2-Difluoro-1,3-benzodioxole-4-carbaldehyde Structure

2,2-Difluoro-1,...

~97%

2,2-Difluoro-4-(hydroxymethyl)-1,3-benzodioxole Structure

2,2-Difluoro-4-...

Formaldehyde Structure

2,2-Difluoro-1,3-benzodioxole Structure

2,2-Difluoro-1,...

~26%

2,2-Difluoro-4-(hydroxymethyl)-1,3-benzodioxole Structure

2,2-Difluoro-4-...

2,2-Difluoro-1,3-benzodioxole Structure

2,2-Difluoro-1,...

Dimethyl sulfate Structure

Dimethyl sulfate

~69%

2,2-difluoro-4-methyl-1,3-benzodioxole Structure

2,2-difluoro-4-...

2,2-Difluoro-1,3-benzodioxole Structure

2,2-Difluoro-1,...

~40%

2,2-Difluoro-1,3-benzodioxol-4-amine Structure

2,2-Difluoro-1,...

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

(2,2-difluoro-1,3-benzodioxol-4-yl)methyl benzenesulfonate Structure

(2,2-difluoro-1...

~73%

2-(2,2-difluoro-2H-1,3-benzodioxol-4-yl)acetonitrile Structure

2-(2,2-difluoro...

2,2-Difluoro-1,3-benzodioxole Structure

2,2-Difluoro-1,...

~%

2-(2,2-difluoro-2H-1,3-benzodioxol-4-yl)acetonitrile Structure

2-(2,2-difluoro...

2,2-Difluoro-1,3-benzodioxole-4-carbaldehyde Structure

2,2-Difluoro-1,...

~%

2-(2,2-difluoro-2H-1,3-benzodioxol-4-yl)acetonitrile Structure

2-(2,2-difluoro...

2,2-Difluoro-4-(hydroxymethyl)-1,3-benzodioxole Structure

2,2-Difluoro-4-...

~%

2-(2,2-difluoro-2H-1,3-benzodioxol-4-yl)acetonitrile Structure

2-(2,2-difluoro...

2,2-difluoro-4-methyl-1,3-benzodioxole Structure

2,2-difluoro-4-...

~%

2-(2,2-difluoro-2H-1,3-benzodioxol-4-yl)acetonitrile Structure

2-(2,2-difluoro...

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

4-(Bromomethyl)-2,2-difluoro-1,3-benzodioxole Structure

4-(Bromomethyl)...

~43%

2-(2,2-difluoro-2H-1,3-benzodioxol-4-yl)acetonitrile Structure

2-(2,2-difluoro...

2,2-difluoro-4-methyl-1,3-benzodioxole Structure

2,2-difluoro-4-...

~66%

4-(Bromomethyl)-2,2-difluoro-1,3-benzodioxole Structure

4-(Bromomethyl)...

2,2-Difluoro-1,3-benzodioxole Structure

2,2-Difluoro-1,...

~%

4-(Bromomethyl)-2,2-difluoro-1,3-benzodioxole Structure

4-(Bromomethyl)...

2,2-Difluoro-1,3-benzodioxole-4-carbaldehyde Structure

2,2-Difluoro-1,...

~%

4-(Bromomethyl)-2,2-difluoro-1,3-benzodioxole Structure

4-(Bromomethyl)...

2,2-difluoro-1,3-benzodioxol-4-carbaldehyde oxime Structure

2,2-difluoro-1,...

~91%

2,2-Difluoro-1,3-benzodioxole-4-carbonitrile Structure

2,2-Difluoro-1,...

2,2-Difluoro-1,3-benzodioxole-4-carbaldehyde Structure

2,2-Difluoro-1,...

~69%

2,2-Difluoro-1,3-benzodioxole-4-carbonitrile Structure

2,2-Difluoro-1,...

2,2-difluoro-1,3-benzodioxole-4-carboxamide Structure

2,2-difluoro-1,...

~91%

2,2-Difluoro-1,3-benzodioxole-4-carbonitrile Structure

2,2-Difluoro-1,...

2,2-Difluoro-1,3-benzodioxole Structure

2,2-Difluoro-1,...

~%

2,2-Difluoro-1,3-benzodioxole-4-carbonitrile Structure

2,2-Difluoro-1,...

2,2-Difluoro-1,3-benzodioxole-4-carboxylic acid Structure

2,2-Difluoro-1,...

~%

2,2-Difluoro-1,3-benzodioxole-4-carbonitrile Structure

2,2-Difluoro-1,...

2,2-Difluoro-1,3-benzodioxole-4-carbonyl chloride Structure

2,2-Difluoro-1,...

~%

2,2-Difluoro-1,3-benzodioxole-4-carbonitrile Structure

2,2-Difluoro-1,...

methyl 2,2-difluoro-1,3-benzodioxole-4-carboxylate Structure

methyl 2,2-difl...

~%

2,2-Difluoro-1,3-benzodioxole-4-carbonitrile Structure

2,2-Difluoro-1,...

2,2-Difluoro-4-(hydroxymethyl)-1,3-benzodioxole Structure

2,2-Difluoro-4-...

~88%

4-(Bromomethyl)-2,2-difluoro-1,3-benzodioxole Structure

4-(Bromomethyl)...