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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Autores principales: Nudelman, N.S., García Liñares, G.E.
Formato: JOUR
Materias:
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
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00223263_v65_n6_p1629_Nudelman
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00223263_v65_n6_p1629_Nudelman
record_format dspace
spelling todo:paper_00223263_v65_n6_p1629_Nudelman2023-10-03T14:31:23Z New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2) Nudelman, N.S. García Liñares, G.E. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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
Nudelman, N.S.
García Liñares, G.E.
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.
format JOUR
author Nudelman, N.S.
García Liñares, G.E.
author_facet Nudelman, N.S.
García Liñares, G.E.
author_sort Nudelman, N.S.
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)
url http://hdl.handle.net/20.500.12110/paper_00223263_v65_n6_p1629_Nudelman
work_keys_str_mv AT nudelmanns newinsightsintothechemistryoflithiumcarbamoylscharacterizationofanadductr2ncocliolinr2
AT garcialinaresge newinsightsintothechemistryoflithiumcarbamoylscharacterizationofanadductr2ncocliolinr2
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