New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2)
Studies of the reaction of lithium dicyclohexylamide with N,N- dibutylformamide, 1-formylpiperidine, and 4-formylmorpholine indicate that the equilibria resulting from these compounds are shifted toward the formation of an adduct, which quickly collapses to dicyclohexylamine and the lithiated carbam...
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2000
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v65_n6_p1629_Nudelman http://hdl.handle.net/20.500.12110/paper_00223263_v65_n6_p1629_Nudelman |
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paper:paper_00223263_v65_n6_p1629_Nudelman2023-06-08T14:49:32Z New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2) 1 formylpiperidine 4 formylmorpholine formamide derivative glyoxylamide lithium dicyclohexylamide n,n dibutylformamide unclassified drug article carbon nuclear magnetic resonance chemical binding chemical reaction kinetics organic chemistry quantitative assay reaction analysis structure analysis Studies of the reaction of lithium dicyclohexylamide with N,N- dibutylformamide, 1-formylpiperidine, and 4-formylmorpholine indicate that the equilibria resulting from these compounds are shifted toward the formation of an adduct, which quickly collapses to dicyclohexylamine and the lithiated carbamoyl anion derived from the initial disubstituted formamide. Further reactions of the lithium carbamoyl lead to a new adduct where a lithiated carbon is bounded to N, O, and a carbonyl functionality. The 13C NMR analysis of the reaction mixtures showed the presence of similar intermediates in all cases: adducts of this type have not been reported before. These dilithiated intermediates were trapped with methyl iodide giving the corresponding doubly methylated derivatives. Isolation of substituted glyoxylamides and quantitative determination of the products yields constitute further evidence of the whole reaction scheme proposed. 2000 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v65_n6_p1629_Nudelman http://hdl.handle.net/20.500.12110/paper_00223263_v65_n6_p1629_Nudelman |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
1 formylpiperidine 4 formylmorpholine formamide derivative glyoxylamide lithium dicyclohexylamide n,n dibutylformamide unclassified drug article carbon nuclear magnetic resonance chemical binding chemical reaction kinetics organic chemistry quantitative assay reaction analysis structure analysis |
| spellingShingle |
1 formylpiperidine 4 formylmorpholine formamide derivative glyoxylamide lithium dicyclohexylamide n,n dibutylformamide unclassified drug article carbon nuclear magnetic resonance chemical binding chemical reaction kinetics organic chemistry quantitative assay reaction analysis structure analysis New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2) |
| topic_facet |
1 formylpiperidine 4 formylmorpholine formamide derivative glyoxylamide lithium dicyclohexylamide n,n dibutylformamide unclassified drug article carbon nuclear magnetic resonance chemical binding chemical reaction kinetics organic chemistry quantitative assay reaction analysis structure analysis |
| description |
Studies of the reaction of lithium dicyclohexylamide with N,N- dibutylformamide, 1-formylpiperidine, and 4-formylmorpholine indicate that the equilibria resulting from these compounds are shifted toward the formation of an adduct, which quickly collapses to dicyclohexylamine and the lithiated carbamoyl anion derived from the initial disubstituted formamide. Further reactions of the lithium carbamoyl lead to a new adduct where a lithiated carbon is bounded to N, O, and a carbonyl functionality. The 13C NMR analysis of the reaction mixtures showed the presence of similar intermediates in all cases: adducts of this type have not been reported before. These dilithiated intermediates were trapped with methyl iodide giving the corresponding doubly methylated derivatives. Isolation of substituted glyoxylamides and quantitative determination of the products yields constitute further evidence of the whole reaction scheme proposed. |
| title |
New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2) |
| title_short |
New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2) |
| title_full |
New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2) |
| title_fullStr |
New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2) |
| title_full_unstemmed |
New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2) |
| title_sort |
new insights into the chemistry of lithium carbamoyls: characterization of an adduct (r2nc(o)cli(oli)nr2) |
| publishDate |
2000 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v65_n6_p1629_Nudelman http://hdl.handle.net/20.500.12110/paper_00223263_v65_n6_p1629_Nudelman |
| _version_ |
1768544765542924288 |