Reactions of nitroanisoles. Part 2. Reactions of 2,4- and 2,6-dinitro-anisole with piperidines in benzene

The reactions of 2,4- (I) and 2,6-dinitroanisole (VIII) with piperidine (II) and N-methylpiperidine (NMP) in benzene have been studied. It was found that (I) and (VIII) react with (II) to give not only the expected aromatic nucleophilic substitution (a.n.s.) products, but also the corresponding dini...

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Autores principales: Nudelman, N.S., Palleros, D.
Formato: JOUR
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_1472779X_v_n7_p995_Nudelman
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_1472779X_v_n7_p995_Nudelman2023-10-03T16:18:06Z Reactions of nitroanisoles. Part 2. Reactions of 2,4- and 2,6-dinitro-anisole with piperidines in benzene Nudelman, N.S. Palleros, D. The reactions of 2,4- (I) and 2,6-dinitroanisole (VIII) with piperidine (II) and N-methylpiperidine (NMP) in benzene have been studied. It was found that (I) and (VIII) react with (II) to give not only the expected aromatic nucleophilic substitution (a.n.s.) products, but also the corresponding dinitrophenols, generated by an SN2 reaction. The rate for each reaction and the overall rates were measured and it was observed that compound (I) has similar rate coefficients for the a.n.s. as well as for the S N2 reaction. Mild acceleration by base was found for the a.n.s. reaction. When (VIII) reacts with (II) the rate of reaction to form 2,6-dinitrophenol is greater than the rate for the a.n.s. In the reaction with NMP only an SN2 reaction was observed. Furthermore, the rates of reaction of (VIII) with (II) and with NMP are ca. 1 000 and 300 times, respectively, the rate of reaction of (I) with these amines. A field effect is proposed for the increase in rate. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_1472779X_v_n7_p995_Nudelman
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
description The reactions of 2,4- (I) and 2,6-dinitroanisole (VIII) with piperidine (II) and N-methylpiperidine (NMP) in benzene have been studied. It was found that (I) and (VIII) react with (II) to give not only the expected aromatic nucleophilic substitution (a.n.s.) products, but also the corresponding dinitrophenols, generated by an SN2 reaction. The rate for each reaction and the overall rates were measured and it was observed that compound (I) has similar rate coefficients for the a.n.s. as well as for the S N2 reaction. Mild acceleration by base was found for the a.n.s. reaction. When (VIII) reacts with (II) the rate of reaction to form 2,6-dinitrophenol is greater than the rate for the a.n.s. In the reaction with NMP only an SN2 reaction was observed. Furthermore, the rates of reaction of (VIII) with (II) and with NMP are ca. 1 000 and 300 times, respectively, the rate of reaction of (I) with these amines. A field effect is proposed for the increase in rate.
format JOUR
author Nudelman, N.S.
Palleros, D.
spellingShingle Nudelman, N.S.
Palleros, D.
Reactions of nitroanisoles. Part 2. Reactions of 2,4- and 2,6-dinitro-anisole with piperidines in benzene
author_facet Nudelman, N.S.
Palleros, D.
author_sort Nudelman, N.S.
title Reactions of nitroanisoles. Part 2. Reactions of 2,4- and 2,6-dinitro-anisole with piperidines in benzene
title_short Reactions of nitroanisoles. Part 2. Reactions of 2,4- and 2,6-dinitro-anisole with piperidines in benzene
title_full Reactions of nitroanisoles. Part 2. Reactions of 2,4- and 2,6-dinitro-anisole with piperidines in benzene
title_fullStr Reactions of nitroanisoles. Part 2. Reactions of 2,4- and 2,6-dinitro-anisole with piperidines in benzene
title_full_unstemmed Reactions of nitroanisoles. Part 2. Reactions of 2,4- and 2,6-dinitro-anisole with piperidines in benzene
title_sort reactions of nitroanisoles. part 2. reactions of 2,4- and 2,6-dinitro-anisole with piperidines in benzene
url http://hdl.handle.net/20.500.12110/paper_1472779X_v_n7_p995_Nudelman
work_keys_str_mv AT nudelmanns reactionsofnitroanisolespart2reactionsof24and26dinitroanisolewithpiperidinesinbenzene
AT pallerosd reactionsofnitroanisolespart2reactionsof24and26dinitroanisolewithpiperidinesinbenzene
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