1429897-06-2Relevant academic research and scientific papers
Stereospecific Suzuki, Sonogashira, and Negishi coupling reactions of N-alkoxyimidoyl iodides and bromides
Dolliver, Debra D.,Bhattarai, Bijay T.,Pandey, Arjun,Lanier, Megan L.,Bordelon, Amber S.,Adhikari, Sarju,Dinser, Jordan A.,Flowers, Patrick F.,Wills, Veronica S.,Schneider, Caroline L.,Shaughnessy, Kevin H.,Moore, Jane N.,Raders, Steven M.,Snowden, Timothy S.,McKim, Artie S.,Fronczek, Frank R.
, p. 3676 - 3687 (2013/06/04)
A high-yielding stereospecific route to the synthesis of single geometric isomers of diaryl oxime ethers through Suzuki coupling of N-alkoxyimidoyl iodides is described. This reaction occurs with complete retention of the imidoyl halide geometry to give single E- or Z-isomers of diaryl oxime ethers. The Sonogashira coupling of N-alkoxyimidoyl iodides and bromides with a wide variety of terminal alkynes to afford single geometric isomers of aryl alkynyl oxime ethers has also been developed. Several of these reactions proceed through copper-free conditions. The Negishi coupling of N-alkoxyimidoyl halides is introduced. The E and Z configurations of nine Suzuki-coupling products and two Sonogashira-coupling products were confirmed by X-ray crystallography.
Synthesis of O-alkylbenzohydroximoyl iodides and a comparison of their structures to other oxime derivatives
Dolliver, Debra D.,Smith, Smitty,Delatte, David B.,Patel, Kavi D.,Thomas, Tiffany E.,Chagnard, Julie,Johnson, James E.,Canseco, Diana C.,Fronczek, Frank R.,Bryan, Clinton D.,Muller, Joann R.,Rowe, Jeffrey E.,McKim, Artie S.
, p. 837 - 846 (2008/09/18)
The first general synthesis of (Z)-O-alkylbenzohydroximidoyl iodides [ArC(I)=NOR] is reported. X-ray crystallographic structures of two of these compounds confirm that they are in the Z-configuration: p-NO2ArC(I)= NOCH3 crystallizes in space group Pnma with lattice constants a = 12.682(2) A, b = 6.5217(15) A, and c = 11.755(2) A, and p-ClArC(I)=NOCH3 crystallizes in space group P21/n with lattice constants a = 15.670(4) A, b = 5.742(4) A, and c = 27.156(7) A and beta angle 102.71(2). Their structures are compared to other O-alkylbenzohydroximoyl halides including p-NO2ArC(F)=NOCH 3 which crystallizes in space group P21/c with lattice constants a = 3.8475(10) A, b = 22.501(5) A, and c = 10.088(2) A and beta angle 91.130(11). The synthesis of two additional compounds containing the N-alkoxyimine moiety {methyl (Z)-O-methyl-4- nitrobenzothiohydroximate [p-NO2ArC(SCH3)=NOCH 3] which crystallizes in space group P21/n with lattice constants a = 11.8046(15) A, b = 7.0774(10) A, and c = 12.2741(15) A and beta angle 100.401(9) and (Z)-O-methyl-4-nitrobenzohydroximoyl azide [p-NO2ArC(N3)=NOCH3] which crystallizes in space group P21/c with lattice constants a = 11.753(2) A, b = 11.310(3) A, and c = 7.351(2) A and beta angle 103.805(15) are also reported. Their structures are compared to (Z)-ethyl benzohydroximate [PhC(OEt)=NOH] and (Z)-O-methyl-4-nitrobenzohydroximoyl cyanide [p-NO 2ArC(CN)=NOCH3] respectively. Characterizations include spectrometric identifications employing IR, 1H-NMR, 13C-NMR and mass spectrometry.
