Syntheses of dialkyl and functionalized ketones via 1-(benzotriazol-1-yl) alkyl methyl thioethers

AR Katritzky, DC Oniciu, I Ghiviriga…

Index: Katritzky, Alan R.; Oniciu, Daniela C.; Ghiviriga, Ion; Soti, Ferenc Journal of Organic Chemistry, 1998 , vol. 63, # 7 p. 2110 - 2115

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Citation Number: 62

Abstract

Benzotriazol-1-ylmethyl methyl thioether (1), after easy deprotonation by BuLi, reacted with alkyl halides to afford 1-(benzotriazol-1-yl) alkyl methyl thioethers 2 in good yields. The utility of compounds 2 as alkanoyl anion equivalents was demonstrated by the reactions of their anions with alkyl halides, aldehydes, ketones, esters, and phenyl isocyanate: the products were readily hydrolyzed to α-functionalized ketones in dilute aqueous acid.

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1-(4-(methylthio)oct-1-en-4-yl)-1H-benzo[d][1,2,3]triazole Structure

203131-89-9

1-(4-(methylthi...

~80%

oct-1-en-4-one Structure

65807-62-7

oct-1-en-4-one

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203131-81-1

N/A

~%

oct-1-en-4-one Structure

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2-Hexanone Structure

591-78-6

2-Hexanone

N/A Structure

203131-81-1

N/A

~%

1-hydroxy-1-phenylhexan-2-one Structure

89393-04-4

1-hydroxy-1-phe...

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203131-81-1

N/A

~%

butyl 4-oxooctanoate Structure

18688-70-5

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2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-(methylthio)-N-phenylhexanamide Structure

203132-02-9

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~49%

2-oxo-N-phenylhexanamide Structure

52884-95-4

2-oxo-N-phenylh...

N/A Structure

203131-81-1

N/A

~%

2-oxo-N-phenylhexanamide Structure

52884-95-4

2-oxo-N-phenylh...

1-(5-(methylthio)nonan-5-yl)-1H-benzo[d][1,2,3]triazole Structure

203131-90-2

1-(5-(methylthi...

~79%

5-Nonanone Structure

502-56-7

5-Nonanone

N/A Structure

203131-81-1

N/A

~%

5-Nonanone Structure

502-56-7

5-Nonanone


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