Identification of products in the reaction of 2-[(hydroxyimino)methyl]-1,3-dimethylimidazolium iodide with diethyl 4-nitrophenyl phosphate in alkaline medium

Verfasser / Beitragende:
[I. Kapitanov, A. Abakumov, A. Serdyuk]
Ort, Verlag, Jahr:
2015
Enthalten in:
Russian Journal of Organic Chemistry, 51/10(2015-10-01), 1368-1375
Format:
Artikel (online)
ID: 605529957
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024 7 0 |a 10.1134/S1070428015100024  |2 doi 
035 |a (NATIONALLICENCE)springer-10.1134/S1070428015100024 
245 0 0 |a Identification of products in the reaction of 2-[(hydroxyimino)methyl]-1,3-dimethylimidazolium iodide with diethyl 4-nitrophenyl phosphate in alkaline medium  |h [Elektronische Daten]  |c [I. Kapitanov, A. Abakumov, A. Serdyuk] 
520 3 |a Products of the reaction of 2-[(hydroxyimino)methyl]-1,3-dimethylimidazolium iodide with diethyl 4-nitrophenyl phosphate in alkaline medium have been identified by electronic spectroscopy, one-(1H, 31P, 13C) and two-dimensional (1H-1H COSY, 1H-31P HMBC) NMR techniques, and NMR titration. 2-[(Hydroxyimino)-methyl]-1,3-dimethylimidazolium iodide has been found to act as nucleophile which is likely to be converted into 2-cyano-1,3-dimethylimidazolium. The other products are 4-nitrophenol and diethyl hydrogen phosphate. Other reaction paths, such as nucleophilic catalysis of the hydrolysis of diethyl 4-nitrophenyl phosphate by 2-[(hydroxyimino)methyl]-1,3-dimethylimidazolium iodide and formation of a stable phosphorylated product, have been ruled out. 
540 |a Pleiades Publishing, Ltd., 2015 
700 1 |a Kapitanov  |D I.  |u Litvinenko Research Institute for Physical Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Kharkovskoe shosse 50, 02160, Kiev, Ukraine  |4 aut 
700 1 |a Abakumov  |D A.  |u Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, pr. Nauki 31, 03028, Kiev, Ukraine  |4 aut 
700 1 |a Serdyuk  |D A.  |u Litvinenko Research Institute for Physical Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Kharkovskoe shosse 50, 02160, Kiev, Ukraine  |4 aut 
773 0 |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/10(2015-10-01), 1368-1375  |x 1070-4280  |q 51:10<1368  |1 2015  |2 51  |o 11178 
856 4 0 |u https://doi.org/10.1134/S1070428015100024  |q text/html  |z Onlinezugriff via DOI 
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900 7 |a Metadata rights reserved  |b Springer special CC-BY-NC licence  |2 nationallicence 
908 |D 1  |a research-article  |2 jats 
949 |B NATIONALLICENCE  |F NATIONALLICENCE  |b NL-springer 
950 |B NATIONALLICENCE  |P 856  |E 40  |u https://doi.org/10.1134/S1070428015100024  |q text/html  |z Onlinezugriff via DOI 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Kapitanov  |D I.  |u Litvinenko Research Institute for Physical Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Kharkovskoe shosse 50, 02160, Kiev, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Abakumov  |D A.  |u Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, pr. Nauki 31, 03028, Kiev, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Serdyuk  |D A.  |u Litvinenko Research Institute for Physical Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Kharkovskoe shosse 50, 02160, Kiev, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/10(2015-10-01), 1368-1375  |x 1070-4280  |q 51:10<1368  |1 2015  |2 51  |o 11178