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

Tetrahedron Letters

A convenient reduction of functionalized polycyclic aromatics into parent hydrocarbons

M Node, K Nishide, K Ohta, E Fujita

Index: Node, Manabu; Nishide, Kiyoharu; Ohta, Keiichiro; Fujita, Eiichi Tetrahedron Letters, 1982 , vol. 23, # 6 p. 689 - 692

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Citation Number: 18

Abstract

Abstract Polycyclic aromatics with various functional group (eg OH, OR, SR, and halogen) were easily defunctionalized by aluminum chloride and ethanethiol to give parent aromatics in high yields under mild conditions. This reaction proceeds through sulfide as the intermediate, hence it is also useful for the synthesis of sulfides of polycyclic aromatics.

9-Bromophenanthrene Structure

9-Bromophenanthrene

Ethanethiol Structure

~48%

Phenanthrene Structure

9-ethylsulfanylphenanthrene Structure

9-ethylsulfanyl...

9-Bromoanthracene Structure

9-Bromoanthracene

Ethanethiol Structure

~48%

Anthracene Structure

9-ethylsulfanylanthracene Structure

9-ethylsulfanyl...

9-Bromoanthracene Structure

9-Bromoanthracene

~0%

Diethyl disulfide Structure

Diethyl disulfide

Anthracene Structure

Anthracene, 9-methoxy- Structure

Anthracene, 9-m...

~0%

Diethyl disulfide Structure

Diethyl disulfide

Anthracene Structure

9-ethoxyanthracene Structure

9-ethoxyanthracene

~0%

Diethyl disulfide Structure

Diethyl disulfide

Anthracene Structure

1-Methoxynapthalene Structure

1-Methoxynapthalene

~0%

Diethyl disulfide Structure

Diethyl disulfide

Naphthalene Structure

9-Bromophenanthrene Structure

9-Bromophenanthrene

~0%

Diethyl disulfide Structure

Diethyl disulfide

Phenanthrene Structure

1-Fluoronaphthalene Structure

1-Fluoronaphthalene

~0%

Diethyl disulfide Structure

Diethyl disulfide

Naphthalene Structure

1-Bromonaphthalene Structure

1-Bromonaphthalene

~0%

Diethyl disulfide Structure

Diethyl disulfide

Naphthalene Structure

9-Methoxyphenanthrene Structure

9-Methoxyphenan...

~0%

Diethyl disulfide Structure

Diethyl disulfide

Phenanthrene Structure

ethyl α-naphthyl sulfide Structure

ethyl α-naphthy...

~0%

Diethyl disulfide Structure

Diethyl disulfide

Naphthalene Structure

N/A Structure

~0%

Diethyl disulfide Structure

Diethyl disulfide

Naphthalene Structure

1-phenoxynaphthalene Structure

1-phenoxynaphthalene

~0%

Diethyl disulfide Structure

Diethyl disulfide

Naphthalene Structure

9-Ethoxyphenanthrene Structure

9-Ethoxyphenanthrene

~0%

Diethyl disulfide Structure

Diethyl disulfide

Phenanthrene Structure

9-ethylsulfanylphenanthrene Structure

9-ethylsulfanyl...

~0%

Diethyl disulfide Structure

Diethyl disulfide

Phenanthrene Structure

1-Naphthalenol Structure

Ethanethiol Structure

~0%

Diethyl disulfide Structure

Diethyl disulfide

Naphthalene Structure

1-Ethoxynaphthalene Structure

1-Ethoxynaphthalene

~0%

Diethyl disulfide Structure

Diethyl disulfide

Naphthalene Structure