The preparation and characterisation of some polynitro derivatives of 2,4,6,-trinitrophenyl substituted naphthalenes
In the present stUdy, the nitration of a number of 2,4,6-trinitrophenyl (picryl) substituted naphthalenes has been conducted. These compounds are: (a) 1-picrylnaphthalene; (b) 2-picrylnaphtha1ene; (c) 1,4- and 1,5-dipicrylnaphthalene; and (d) 1-methyl-4-picrylnaphthalene, all these compound being pr...
Main Author: | |
---|---|
Published: |
Kingston University
1979
|
Online Access: | https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.554957 |
id |
ndltd-bl.uk-oai-ethos.bl.uk-554957 |
---|---|
record_format |
oai_dc |
spelling |
ndltd-bl.uk-oai-ethos.bl.uk-5549572019-01-29T03:19:10ZThe preparation and characterisation of some polynitro derivatives of 2,4,6,-trinitrophenyl substituted naphthalenesBergman, J. S.1979In the present stUdy, the nitration of a number of 2,4,6-trinitrophenyl (picryl) substituted naphthalenes has been conducted. These compounds are: (a) 1-picrylnaphthalene; (b) 2-picrylnaphtha1ene; (c) 1,4- and 1,5-dipicrylnaphthalene; and (d) 1-methyl-4-picrylnaphthalene, all these compound being produced by Ullmann reaction between picryl chloride and the halogen substituted naphthalenes. A large number- of nitro-derivatives have been isolated and the structures assigned on the basis of nmr and mass spectral data. Some nitro -derivatives were also assigned on the basis of unequivocal synthesis from known compounds. The,most highly nitrated compounds isolated were from the nitration of 1,4- and 1,5-dipicrylnaphthalenes, where it was found that by using extremely vigourous conditions, three more nitro-groups could be introduced into the naphthalene moiety, making the total number of nitro-groups on the four rings, nine in all. The stability of these highly nitrated compounds to oxidation is in accord with an incomplete previous study of 1-picrylnaphthalene. The nitration of picrylbenzene has been previously studied, and a mechanism was proposed to explain the proportion of each isomer in the product mixture. This mechanism involved the stabilization of the p-nitropicrylbenzene (the predominant isomer) by a field effect involving the oxygen atoms of the ortho-nitro-groups. This mechanism is commented upon with particular reference to the nitration of picryl substituted naphthalenes of the present study.Kingston Universityhttps://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.554957http://eprints.kingston.ac.uk/20467/Electronic Thesis or Dissertation |
collection |
NDLTD |
sources |
NDLTD |
description |
In the present stUdy, the nitration of a number of 2,4,6-trinitrophenyl (picryl) substituted naphthalenes has been conducted. These compounds are: (a) 1-picrylnaphthalene; (b) 2-picrylnaphtha1ene; (c) 1,4- and 1,5-dipicrylnaphthalene; and (d) 1-methyl-4-picrylnaphthalene, all these compound being produced by Ullmann reaction between picryl chloride and the halogen substituted naphthalenes. A large number- of nitro-derivatives have been isolated and the structures assigned on the basis of nmr and mass spectral data. Some nitro -derivatives were also assigned on the basis of unequivocal synthesis from known compounds. The,most highly nitrated compounds isolated were from the nitration of 1,4- and 1,5-dipicrylnaphthalenes, where it was found that by using extremely vigourous conditions, three more nitro-groups could be introduced into the naphthalene moiety, making the total number of nitro-groups on the four rings, nine in all. The stability of these highly nitrated compounds to oxidation is in accord with an incomplete previous study of 1-picrylnaphthalene. The nitration of picrylbenzene has been previously studied, and a mechanism was proposed to explain the proportion of each isomer in the product mixture. This mechanism involved the stabilization of the p-nitropicrylbenzene (the predominant isomer) by a field effect involving the oxygen atoms of the ortho-nitro-groups. This mechanism is commented upon with particular reference to the nitration of picryl substituted naphthalenes of the present study. |
author |
Bergman, J. S. |
spellingShingle |
Bergman, J. S. The preparation and characterisation of some polynitro derivatives of 2,4,6,-trinitrophenyl substituted naphthalenes |
author_facet |
Bergman, J. S. |
author_sort |
Bergman, J. S. |
title |
The preparation and characterisation of some polynitro derivatives of 2,4,6,-trinitrophenyl substituted naphthalenes |
title_short |
The preparation and characterisation of some polynitro derivatives of 2,4,6,-trinitrophenyl substituted naphthalenes |
title_full |
The preparation and characterisation of some polynitro derivatives of 2,4,6,-trinitrophenyl substituted naphthalenes |
title_fullStr |
The preparation and characterisation of some polynitro derivatives of 2,4,6,-trinitrophenyl substituted naphthalenes |
title_full_unstemmed |
The preparation and characterisation of some polynitro derivatives of 2,4,6,-trinitrophenyl substituted naphthalenes |
title_sort |
preparation and characterisation of some polynitro derivatives of 2,4,6,-trinitrophenyl substituted naphthalenes |
publisher |
Kingston University |
publishDate |
1979 |
url |
https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.554957 |
work_keys_str_mv |
AT bergmanjs thepreparationandcharacterisationofsomepolynitroderivativesof246trinitrophenylsubstitutednaphthalenes AT bergmanjs preparationandcharacterisationofsomepolynitroderivativesof246trinitrophenylsubstitutednaphthalenes |
_version_ |
1718968256561152000 |