2015
DOI: 10.1080/00397911.2015.1061672
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Using N-Nitrosodichloroacetamides to Conveniently Convert Linear Primary Amines into Alcohols

Abstract: The reported rearrangement of N-nitrosodichloroacetamides provides a practical method for converting primary amines into primary alcohols. The reaction sequence is operationally simple, only requires a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.

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Cited by 6 publications
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“…Melting point analyses were carried out with a SMP3 Bibbi Stuart Scientific system. (But-3-yn-1-yloxy)triisopropylsilane 2 , 55 benzyl 6-aminohexanoate 11 , 56 6-(2-(4,7,10-tris(2-( tert -butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)hexanoic acid (DOTAMA-C 6 -COOH, 16 ) 57 were synthesized as described in literature and their spectroscopic data corresponded with those reported. MR image was acquired on a Bruker Avance Neo 300 MHz spectrometer (7 T) equipped with a Micro 2.5 microimaging probe (Bruker BioSpin, Ettlingen, Germany).…”
Section: Methodsmentioning
confidence: 99%
“…Melting point analyses were carried out with a SMP3 Bibbi Stuart Scientific system. (But-3-yn-1-yloxy)triisopropylsilane 2 , 55 benzyl 6-aminohexanoate 11 , 56 6-(2-(4,7,10-tris(2-( tert -butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)hexanoic acid (DOTAMA-C 6 -COOH, 16 ) 57 were synthesized as described in literature and their spectroscopic data corresponded with those reported. MR image was acquired on a Bruker Avance Neo 300 MHz spectrometer (7 T) equipped with a Micro 2.5 microimaging probe (Bruker BioSpin, Ettlingen, Germany).…”
Section: Methodsmentioning
confidence: 99%