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

A new rearrangement of alkoxybenzyl anions

…, TJ Siahaan, K Suvannachut

Index: Bates, Robert B.; Siahaan, Teruna J.; Suvannachut, Kessara Journal of Organic Chemistry, 1990 , vol. 55, # 4 p. 1328 - 1334

Full Text: HTML

Citation Number: 15

Abstract

Alkyl groups migrate from oxygen to carbon in alkyl aryl ethers which have been metalated in benzylic positions. 2, 6-Dimethylanisole provides a variety of 2, 6-dialkylphenols and their ethers in 45-80% yields. Rearrangement products are obtained in 10-30% yields from other dimethylanisoles and from methylanisoles. The reactions appear to proceed, like Wittig rearrangements, by homolytic cleavage of the alkyl-oxygen bond followed by ...

Diethyl sulfate Structure

Diethyl sulfate

2,4-dimethylanisole Structure

2,4-dimethylanisole

~%

p-Cresol, 2-propyl- Structure

p-Cresol, 2-propyl-

N/A Structure

Detail

Diethyl sulfate Structure

Diethyl sulfate

2-Methylanisole Structure

2-Methylanisole

~%

1-ethoxy-2-ethylbenzene Structure

1-ethoxy-2-ethy...

1-Methoxy-2-propylbenzene Structure

1-Methoxy-2-pro...

Detail

Diethyl sulfate Structure

Diethyl sulfate

2-Methylanisole Structure

2-Methylanisole

~%

1-ethoxy-2-ethylbenzene Structure

1-ethoxy-2-ethy...

1-Methoxy-2-propylbenzene Structure

1-Methoxy-2-pro...

Detail

Diethyl sulfate Structure

Diethyl sulfate

2,6-Dimethylanisole Structure

2,6-Dimethylanisole

~%

Benzene,2-ethoxy-1,3-dimethyl- Structure

Benzene,2-ethox...

N/A Structure

Detail

Diethyl sulfate Structure

Diethyl sulfate

2-Methylanisole Structure

2-Methylanisole

~%

1-ethoxy-2-ethylbenzene Structure

1-ethoxy-2-ethy...

1-Methoxy-2-propylbenzene Structure

1-Methoxy-2-pro...

Detail

Diethyl sulfate Structure

Diethyl sulfate

2-Methylanisole Structure

2-Methylanisole

~%

o-Ethoxytoluene Structure

o-Ethoxytoluene

1-ethoxy-2-ethylbenzene Structure

1-ethoxy-2-ethy...

Detail

Diethyl sulfate Structure

Diethyl sulfate

2-Methylanisole Structure

2-Methylanisole

~%

1-ethoxy-2-ethylbenzene Structure

1-ethoxy-2-ethy...

1-Methoxy-2-propylbenzene Structure

1-Methoxy-2-pro...

Detail

Diethyl sulfate Structure

Diethyl sulfate

1-Methoxy-2,3-dimethylbenzene Structure

1-Methoxy-2,3-d...

~%

1-ethoxy-2,3-dimethylbenzene Structure

1-ethoxy-2,3-di...

N/A Structure

Detail

2,6-Dimethylanisole Structure

2,6-Dimethylanisole

~%

2,6-Xylenol Structure

2-ETHYL-6-METHYLPHENOL Structure

2-ETHYL-6-METHY...

Phenol,2-methyl-6-propyl- Structure

Phenol,2-methyl...

Benzene,2-ethoxy-1,3-dimethyl- Structure

Benzene,2-ethox...

~%

2,6-Xylenol Structure

2-ETHYL-6-METHYLPHENOL Structure

2-ETHYL-6-METHY...

Phenol,2-methyl-6-propyl- Structure

Phenol,2-methyl...

Detail

Benzene,2-ethoxy-1,3-dimethyl- Structure

Benzene,2-ethox...

Anisole Structure

~%

2,6-Xylenol Structure

2-ETHYL-6-METHYLPHENOL Structure

2-ETHYL-6-METHY...

Detail

Diethyl sulfate Structure

Diethyl sulfate

4-Methylanisole Structure

4-Methylanisole

~%

Benzene,1-ethoxy-4-methyl- Structure

Benzene,1-ethox...

para-ethyl phenetole Structure

para-ethyl phenetole

Detail

Diethyl sulfate Structure

Diethyl sulfate

4-Methoxy-1,2-dimethylbenzene Structure

4-Methoxy-1,2-d...

~%

4-methyl-3-propylphenol Structure

4-methyl-3-prop...

3,4-DIMETHYLPHENETOLE Structure

3,4-DIMETHYLPHE...

Detail

Diethyl sulfate Structure

Diethyl sulfate

4-Methoxy-1,2-dimethylbenzene Structure

4-Methoxy-1,2-d...

~%

4-methyl-3-propylphenol Structure

4-methyl-3-prop...

N/A Structure

Detail

Diethyl sulfate Structure

Diethyl sulfate

4-Methoxy-1,2-dimethylbenzene Structure

4-Methoxy-1,2-d...

~%

4-methyl-3-propylphenol Structure

4-methyl-3-prop...

N/A Structure

Detail

Diethyl sulfate Structure

Diethyl sulfate

3-Methylanisole Structure

3-Methylanisole

~%

1-methoxy-3-propylbenzene Structure

1-methoxy-3-pro...

N/A Structure

Diethyl sulfate Structure

Diethyl sulfate

3-Methylanisole Structure

3-Methylanisole

~%

Benzene, 1-ethoxy-3-methyl- Structure

Benzene, 1-etho...

3-Ethylphenylethyl ether Structure

3-Ethylphenylet...

Detail

Diethyl sulfate Structure

Diethyl sulfate

2-Methylanisole Structure

2-Methylanisole

~%

1-ethoxy-2-ethylbenzene Structure

1-ethoxy-2-ethy...

1-Methoxy-2-propylbenzene Structure

1-Methoxy-2-pro...

Detail

Diethyl sulfate Structure

Diethyl sulfate

2-Methylanisole Structure

2-Methylanisole

~%

1-ethoxy-2-ethylbenzene Structure

1-ethoxy-2-ethy...

1-Methoxy-2-propylbenzene Structure

1-Methoxy-2-pro...

Detail

Diethyl sulfate Structure

Diethyl sulfate

4-Methylanisole Structure

4-Methylanisole

~%

Benzene,1-ethoxy-4-methyl- Structure

Benzene,1-ethox...

4-n-propylanisole Structure

4-n-propylanisole

Detail

Diethyl sulfate Structure

Diethyl sulfate

2-Methoxy-1,4-dimethylbenzene Structure

2-Methoxy-1,4-d...

~%

5-methyl-2-propyl-phenol Structure

5-methyl-2-prop...

N/A Structure

Detail

Diethyl sulfate Structure

Diethyl sulfate

2-Methylanisole Structure

2-Methylanisole

~%

o-Ethoxytoluene Structure

o-Ethoxytoluene

1-ethoxy-2-ethylbenzene Structure

1-ethoxy-2-ethy...

Detail

Diethyl sulfate Structure

Diethyl sulfate

4-Methoxy-1,2-dimethylbenzene Structure

4-Methoxy-1,2-d...

~%

4-methyl-3-propylphenol Structure

4-methyl-3-prop...

3,4-DIMETHYLPHENETOLE Structure

3,4-DIMETHYLPHE...

Detail

Diethyl sulfate Structure

Diethyl sulfate

4-Methylanisole Structure

4-Methylanisole

~%

Benzene,1-ethoxy-4-methyl- Structure

Benzene,1-ethox...

para-ethyl phenetole Structure

para-ethyl phenetole

Detail

Benzene,2-ethoxy-1,3-dimethyl- Structure

Benzene,2-ethox...

Dimethyl sulfate Structure

Dimethyl sulfate

~%

1,3-diethyl-2-methoxybenzene Structure

1,3-diethyl-2-m...

N/A Structure

Detail

Benzene,2-ethoxy-1,3-dimethyl- Structure

Benzene,2-ethox...

Dimethyl sulfate Structure

Dimethyl sulfate

~%

1,3-diethyl-2-methoxybenzene Structure

1,3-diethyl-2-m...

N/A Structure

Detail

Benzene,2-ethoxy-1,3-dimethyl- Structure

Benzene,2-ethox...

Dimethyl sulfate Structure

Dimethyl sulfate

~%

1,3-diethyl-2-methoxybenzene Structure

1,3-diethyl-2-m...

N/A Structure

Detail

Benzene,2-ethoxy-1,3-dimethyl- Structure

Benzene,2-ethox...

Dimethyl sulfate Structure

Dimethyl sulfate

~%

1,3-diethyl-2-methoxybenzene Structure

1,3-diethyl-2-m...

N/A Structure

Detail

Benzene,2-ethoxy-1,3-dimethyl- Structure

Benzene,2-ethox...

Dimethyl sulfate Structure

Dimethyl sulfate

~%

1,3-diethyl-2-methoxybenzene Structure

1,3-diethyl-2-m...

N/A Structure

Detail

Benzene,2-ethoxy-1,3-dimethyl- Structure

Benzene,2-ethox...

Dimethyl sulfate Structure

Dimethyl sulfate

~%

2,6-Dimethylanisole Structure

2,6-Dimethylanisole

1,3-diethyl-2-methoxybenzene Structure

1,3-diethyl-2-m...

Detail

Säurekatalysierte Umlagerung von Allyl??cyclohexadienon??tos...

[Schmid,M. et al. Helvetica Chimica Acta, 1971 , vol. 54, p. 937 - 951]

Säurekatalysierte Umlagerung von Allyl??cyclohexadienon??tos...

[Schmid,M. et al. Helvetica Chimica Acta, 1971 , vol. 54, p. 937 - 951]

Säurekatalysierte Umlagerung von Allyl??cyclohexadienon??tos...

[Schmid,M. et al. Helvetica Chimica Acta, 1971 , vol. 54, p. 937 - 951]

The Pyrolysis of Allyl 2, 4, 6-Trialkylphenyl Ethers

[Hurd; Yarnall Journal of the American Chemical Society, 1937 , vol. 59, p. 1686,1688]

The Pyrolysis of Allyl 2, 4, 6-Trialkylphenyl Ethers

[Hurd; Yarnall Journal of the American Chemical Society, 1937 , vol. 59, p. 1686,1688]