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

Tetrahedron

Synthesis of α-selenoalkyllithium compounds

…, W Dumont, M Clarembeau, G Bernard, E Badaoui

Index: Krief, A.; Dumont, W.; Clarembeau, M.; Bernard, G.; Badaoui, E. Tetrahedron, 1989 , vol. 45, # 7 p. 2005 - 2022

Full Text: HTML

Citation Number: 111

Abstract

α-Phenylselenoalkyllithiums and α-methylselenoalkyllithiums have been prepared from the corresponding selenoacetals and alkyllithiums. Several features of this reaction are disclosed. For example, the reaction is more readily achieved on phenylselenoacetals than on methylseleno analogues. Those derived from hindered carbonyl compounds are less readily cleaved. s-BuLi/THF proved superior to n-BuLi in THF, itself better than n-BuLi in ...

Benzenethiol, potassium salt Structure

Benzenethiol, p...

~%

methylselanylbenzene Structure

methylselanylbenzene

phenylselanylmethylselanylbenzene Structure

phenylselanylme...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

methylselanylbenzene Structure

methylselanylbenzene

Detail

1-Bromodecane Structure

((methylselanyl)methyl)lithium Structure

((methylselanyl...

~2%

1-methylselanyldecane Structure

1-methylselanyl...

1-methylselanylundecane Structure

1-methylselanyl...

Diiodomethane Structure

potassium methanethiolate Structure

potassium metha...

~%

bis(methylselanyl)methane Structure

bis(methylselan...

1-Bromodecane Structure

lithium,methanidylselanylbenzene Structure

lithium,methani...

~2%

decylselanylbenzene Structure

decylselanylbenzene

N/A Structure

Benzaldehyde Structure

1,1-bis(methylseleno)-2-methylcyclohexane Structure

1,1-bis(methyls...

~%

2-methylselanylbutane Structure

2-methylselanyl...

N/A Structure

Benzaldehyde Structure

2,2-bis(methylseleno)adamantane Structure

2,2-bis(methyls...

~%

2-methylselanylbutane Structure

2-methylselanyl...

N/A Structure

1-Bromodecane Structure

((methylselanyl)methyl)lithium Structure

((methylselanyl...

~87%

1-methylselanyldecane Structure

1-methylselanyl...

1-methylselanylundecane Structure

1-methylselanyl...

N/A Structure

Benzaldehyde Structure

~%

butan-2-ylselanylbenzene Structure

butan-2-ylselan...

1,2-diphenyl-2-methylseleno-ethane-1-ol Structure

1,2-diphenyl-2-...

1,1-bis(phenylselenenyl)-2-methylcyclohexane Structure

1,1-bis(phenyls...

Benzaldehyde Structure

~%

butan-2-ylselanylbenzene Structure

butan-2-ylselan...

phenyl-[(1-phenylseleno-2-methyl)cyclohexyl]-methanol Structure

phenyl-[(1-phen...

Benzenethiol, potassium salt Structure

Benzenethiol, p...

~%

butylselanylbenzene Structure

butylselanylbenzene

1,1-bis(phenylselenenyl)-4-tert-butylcyclohexane Structure

1,1-bis(phenyls...

~%

butylselanylbenzene Structure

butylselanylbenzene

trans-1-phenylselenenyl-4-tert-butylcyclohexane Structure

trans-1-phenyls...

1,1-bis(phenylselenenyl)-2-methylcyclohexane Structure

1,1-bis(phenyls...

~%

butylselanylbenzene Structure

butylselanylbenzene

N/A Structure

phenylselanylmethylselanylbenzene Structure

phenylselanylme...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

1-phenyl-2-(phenylselanyl)ethanol Structure

1-phenyl-2-(phe...

1-phenylselanylethylselanylbenzene Structure

1-phenylselanyl...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

1-phenyl-2-phenylselanyl-propan-1-ol Structure

1-phenyl-2-phen...

1-phenylselanylheptylselanylbenzene Structure

1-phenylselanyl...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

N/A Structure

2,2-bis (phenylseleno)propane Structure

2,2-bis (phenyl...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

2-Methyl-1-phenyl-2-phenylseleno-1-propanol Structure

2-Methyl-1-phen...

(1-phenylselanylcyclopentyl)selanylbenzene Structure

(1-phenylselany...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

phenyl-[(1-phenylseleno)cyclopentyl]-methanol Structure

phenyl-[(1-phen...

1,1-bis(phenylselenenyl)cyclohexane Structure

1,1-bis(phenyls...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

phenyl-[(1-phenylseleno)cyclohexyl]-methanol Structure

phenyl-[(1-phen...

1-phenyl-1,1-bis(phenylseleno)ethane Structure

1-phenyl-1,1-bi...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

1,2-diphenyl-2-methylseleno-propane-1-ol Structure

1,2-diphenyl-2-...

1,1-bis(phenylselenenyl)-4-tert-butylcyclohexane Structure

1,1-bis(phenyls...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

N/A Structure

7-phenylselanyltridecan-7-ylselanylbenzene Structure

7-phenylselanyl...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

N/A Structure

1,1-(bisphenylseleno)cyclopropane Structure

1,1-(bisphenyls...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

phenyl-[(1-phenylseleno)cyclopropyl]-methanol Structure

phenyl-[(1-phen...

bis(phenylselanyl)methylbenzene Structure

bis(phenylselan...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

N/A Structure

1-phenylselanylpropylselanylbenzene Structure

1-phenylselanyl...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

1-phenyl-2-phenylselenobutane-1-ol Structure

1-phenyl-2-phen...

1,1-bis(phenylseleno)cyclobutane Structure

1,1-bis(phenyls...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

phenyl-[(1-phenylseleno)cyclobutyl]-methanol Structure

phenyl-[(1-phen...

Benzaldehyde Structure

1,1-bis(phenylseleno)-2,2-dimethyl-propane Structure

1,1-bis(phenyls...

~%

butylselanylbenzene Structure

butylselanylbenzene

1-phenyl-2-phenylseleno-3,3-dimethyl-butane-1-ol Structure

1-phenyl-2-phen...

Benzaldehyde Structure

2,2-bis(phenylseleno)-3,3-dimethyl-butane Structure

2,2-bis(phenyls...

~%

butylselanylbenzene Structure

butylselanylbenzene

1-phenyl-2-phenylseleno-2,3,3-trimethyl-butane-1-ol Structure

1-phenyl-2-phen...

Benzaldehyde Structure

2,2-bis(phenylselenyl) octane Structure

2,2-bis(phenyls...

~%

butylselanylbenzene Structure

butylselanylbenzene

N/A Structure

phenylselanylmethylselanylbenzene Structure

phenylselanylme...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

methylselanylbenzene Structure

methylselanylbenzene

Detail

1-phenylselanylheptylselanylbenzene Structure

1-phenylselanyl...

Benzaldehyde Structure

~%

butylselanylbenzene Structure

butylselanylbenzene

1-phenyl-2,2-bis(phenylselanyl)octan-1-ol Structure

1-phenyl-2,2-bi...

Detail

Diiodomethane Structure

Benzenethiol, potassium salt Structure

Benzenethiol, p...

~%

phenylselanylmethylselanylbenzene Structure

phenylselanylme...

A novel and highly efficient synthetic route to unsymmetrica...

[Cohen, Richard J.; Fox, Daniel L.; Salvatore, Ralph Nicholas Journal of Organic Chemistry, 2004 , vol. 69, # 12 p. 4265 - 4268]

Nucleophilic cleavage of lactones and esters with zinc selen...

[Nazari, Mohammad; Movassagh, Barahman Tetrahedron Letters, 2009 , vol. 50, # 4 p. 438 - 441]

Nucleophilic cleavage of lactones and esters with zinc selen...

[Nazari, Mohammad; Movassagh, Barahman Tetrahedron Letters, 2009 , vol. 50, # 4 p. 438 - 441]

Nucleophilic cleavage of lactones and esters with zinc selen...

[Nazari, Mohammad; Movassagh, Barahman Tetrahedron Letters, 2009 , vol. 50, # 4 p. 438 - 441]

Nucleophilic cleavage of lactones and esters with zinc selen...

[Nazari, Mohammad; Movassagh, Barahman Tetrahedron Letters, 2009 , vol. 50, # 4 p. 438 - 441]