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Synthesis and structural studies of a new class of quaternary ammonium salts, which are derivatives of cage adamanzane type aminal 1, 3, 6, 8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU)
BACKGROUND: Novel mono N-alkyl quaternary ammonium salts (3a-f) were prepared using the Menschutkin reaction from the cage adamanzane type aminal 1,3,6,8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU) and alkyl iodides, such as methyl, ethyl, propyl, butyl, pentyl and hexyl iodide (2a-f), in dry acet...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
BioMed Central
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3189110/ https://www.ncbi.nlm.nih.gov/pubmed/21933409 http://dx.doi.org/10.1186/1752-153X-5-55 |
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author | Rivera, Augusto Sadat-Bernal, John Ríos-Motta, Jaime Dušek, Michal Palatinus, Lukáš |
author_facet | Rivera, Augusto Sadat-Bernal, John Ríos-Motta, Jaime Dušek, Michal Palatinus, Lukáš |
author_sort | Rivera, Augusto |
collection | PubMed |
description | BACKGROUND: Novel mono N-alkyl quaternary ammonium salts (3a-f) were prepared using the Menschutkin reaction from the cage adamanzane type aminal 1,3,6,8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU) and alkyl iodides, such as methyl, ethyl, propyl, butyl, pentyl and hexyl iodide (2a-f), in dry acetonitrile at room temperature. RESULTS: The structures of these new quaternary ammonium salts were established using various spectral and electrospray ionization mass spectrometry (ESI-MS) analyses. Compound (3b) was also analyzed using X-ray crystallography. CONCLUSION: It was noted that alkyl chain length did not significantly affect the reaction because all employed alkyl iodide electrophiles reacted in a similar fashion with the aminal 1 to produce the corresponding mono N-quaternary ammonium salts, which were characterized by spectroscopic and analytical techniques. |
format | Online Article Text |
id | pubmed-3189110 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | BioMed Central |
record_format | MEDLINE/PubMed |
spelling | pubmed-31891102011-10-08 Synthesis and structural studies of a new class of quaternary ammonium salts, which are derivatives of cage adamanzane type aminal 1, 3, 6, 8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU) Rivera, Augusto Sadat-Bernal, John Ríos-Motta, Jaime Dušek, Michal Palatinus, Lukáš Chem Cent J Research Article BACKGROUND: Novel mono N-alkyl quaternary ammonium salts (3a-f) were prepared using the Menschutkin reaction from the cage adamanzane type aminal 1,3,6,8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU) and alkyl iodides, such as methyl, ethyl, propyl, butyl, pentyl and hexyl iodide (2a-f), in dry acetonitrile at room temperature. RESULTS: The structures of these new quaternary ammonium salts were established using various spectral and electrospray ionization mass spectrometry (ESI-MS) analyses. Compound (3b) was also analyzed using X-ray crystallography. CONCLUSION: It was noted that alkyl chain length did not significantly affect the reaction because all employed alkyl iodide electrophiles reacted in a similar fashion with the aminal 1 to produce the corresponding mono N-quaternary ammonium salts, which were characterized by spectroscopic and analytical techniques. BioMed Central 2011-09-20 /pmc/articles/PMC3189110/ /pubmed/21933409 http://dx.doi.org/10.1186/1752-153X-5-55 Text en Copyright ©2011 Rivera., et al |
spellingShingle | Research Article Rivera, Augusto Sadat-Bernal, John Ríos-Motta, Jaime Dušek, Michal Palatinus, Lukáš Synthesis and structural studies of a new class of quaternary ammonium salts, which are derivatives of cage adamanzane type aminal 1, 3, 6, 8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU) |
title | Synthesis and structural studies of a new class of quaternary ammonium salts, which are derivatives of cage adamanzane type aminal 1, 3, 6, 8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU) |
title_full | Synthesis and structural studies of a new class of quaternary ammonium salts, which are derivatives of cage adamanzane type aminal 1, 3, 6, 8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU) |
title_fullStr | Synthesis and structural studies of a new class of quaternary ammonium salts, which are derivatives of cage adamanzane type aminal 1, 3, 6, 8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU) |
title_full_unstemmed | Synthesis and structural studies of a new class of quaternary ammonium salts, which are derivatives of cage adamanzane type aminal 1, 3, 6, 8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU) |
title_short | Synthesis and structural studies of a new class of quaternary ammonium salts, which are derivatives of cage adamanzane type aminal 1, 3, 6, 8-tetraazatricyclo[4.3.1.1(3,8)]undecane (TATU) |
title_sort | synthesis and structural studies of a new class of quaternary ammonium salts, which are derivatives of cage adamanzane type aminal 1, 3, 6, 8-tetraazatricyclo[4.3.1.1(3,8)]undecane (tatu) |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3189110/ https://www.ncbi.nlm.nih.gov/pubmed/21933409 http://dx.doi.org/10.1186/1752-153X-5-55 |
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