<!DOCTYPE article
PUBLIC "-//NLM//DTD JATS (Z39.96) Journal Publishing DTD v1.4 20190208//EN"
       "JATS-journalpublishing1.dtd">
<article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" article-type="research-article" dtd-version="1.4" xml:lang="en">
 <front>
  <journal-meta>
   <journal-id journal-id-type="publisher-id">From Chemistry Towards Technology Step-By-Step</journal-id>
   <journal-title-group>
    <journal-title xml:lang="en">From Chemistry Towards Technology Step-By-Step</journal-title>
    <trans-title-group xml:lang="ru">
     <trans-title>От химии к технологии шаг за шагом</trans-title>
    </trans-title-group>
   </journal-title-group>
   <issn publication-format="online">2782-1900</issn>
  </journal-meta>
  <article-meta>
   <article-id pub-id-type="publisher-id">81565</article-id>
   <article-id pub-id-type="doi">10.52957/27821900_2023_01_117</article-id>
   <article-categories>
    <subj-group subj-group-type="toc-heading" xml:lang="ru">
     <subject>Научные статьи</subject>
    </subj-group>
    <subj-group subj-group-type="toc-heading" xml:lang="en">
     <subject>Scientific articles</subject>
    </subj-group>
    <subj-group>
     <subject>Научные статьи</subject>
    </subj-group>
   </article-categories>
   <title-group>
    <article-title xml:lang="en">Orientation of benzophenone dinitro derivatives mono-reduction</article-title>
    <trans-title-group xml:lang="ru">
     <trans-title>Orientation of benzophenone dinitro derivatives mono-reduction</trans-title>
    </trans-title-group>
   </title-group>
   <contrib-group content-type="authors">
    <contrib contrib-type="author">
     <name-alternatives>
      <name xml:lang="ru">
       <surname>Богданова</surname>
       <given-names>Дарья Михайловна</given-names>
      </name>
      <name xml:lang="en">
       <surname>Bogdanova</surname>
       <given-names>Daria Mikhaylovna</given-names>
      </name>
     </name-alternatives>
     <xref ref-type="aff" rid="aff-1"/>
    </contrib>
    <contrib contrib-type="author">
     <name-alternatives>
      <name xml:lang="ru">
       <surname>Савина</surname>
       <given-names>Луиза Ильинична</given-names>
      </name>
      <name xml:lang="en">
       <surname>Savina</surname>
       <given-names>Luisa Ilyinichna</given-names>
      </name>
     </name-alternatives>
     <email>luizasavina2000@mail.ru</email>
     <xref ref-type="aff" rid="aff-2"/>
     <xref ref-type="aff" rid="aff-1"/>
    </contrib>
    <contrib contrib-type="author">
     <name-alternatives>
      <name xml:lang="ru">
       <surname>Бегунов</surname>
       <given-names>Роман Сергеевич</given-names>
      </name>
      <name xml:lang="en">
       <surname>Begunov</surname>
       <given-names>Roman Sergeevich</given-names>
      </name>
     </name-alternatives>
     <email>begunov@bio.ac.ru</email>
     <bio xml:lang="ru">
      <p>кандидат химических наук;</p>
     </bio>
     <bio xml:lang="en">
      <p>candidate of chemical sciences;</p>
     </bio>
     <xref ref-type="aff" rid="aff-2"/>
     <xref ref-type="aff" rid="aff-1"/>
    </contrib>
   </contrib-group>
   <aff-alternatives id="aff-1">
    <aff>
     <institution xml:lang="ru">Ярославский государственный университет им. П.Г. Демидова</institution>
    </aff>
    <aff>
     <institution xml:lang="en">P.G. Demidov Yaroslavl State University</institution>
    </aff>
   </aff-alternatives>
   <aff-alternatives id="aff-2">
    <aff>
     <institution xml:lang="ru">Ярославский государственный медицинский университет</institution>
    </aff>
    <aff>
     <institution xml:lang="en">Yaroslavl State Medical University</institution>
    </aff>
   </aff-alternatives>
   <pub-date publication-format="print" date-type="pub" iso-8601-date="2023-03-23T00:00:00+03:00">
    <day>23</day>
    <month>03</month>
    <year>2023</year>
   </pub-date>
   <pub-date publication-format="electronic" date-type="pub" iso-8601-date="2023-03-23T00:00:00+03:00">
    <day>23</day>
    <month>03</month>
    <year>2023</year>
   </pub-date>
   <volume>4</volume>
   <issue>1</issue>
   <fpage>117</fpage>
   <lpage>123</lpage>
   <history>
    <date date-type="received" iso-8601-date="2023-03-01T00:00:00+03:00">
     <day>01</day>
     <month>03</month>
     <year>2023</year>
    </date>
    <date date-type="accepted" iso-8601-date="2023-03-22T00:00:00+03:00">
     <day>22</day>
     <month>03</month>
     <year>2023</year>
    </date>
   </history>
   <self-uri xlink:href="https://chemintech.ru/en/nauka/article/81565/view">https://chemintech.ru/en/nauka/article/81565/view</self-uri>
   <abstract xml:lang="ru">
    <p>The paper presents a study of monoreduction selectivity process of 3,4'-NO2-4-R-benzophenones containing different functional groups. The presence of an electron-accepting substituent in the ortho-position of the nitro group facilitated its reduction, while electron-donating and bulk functional groups prevented it.</p>
   </abstract>
   <trans-abstract xml:lang="en">
    <p>The paper presents a study of monoreduction selectivity process of 3,4'-NO2-4-R-benzophenones containing different functional groups. The presence of an electron-accepting substituent in the ortho-position of the nitro group facilitated its reduction, while electron-donating and bulk functional groups prevented it.</p>
   </trans-abstract>
   <kwd-group xml:lang="en">
    <kwd>Mono-reduction</kwd>
    <kwd>selectivity</kwd>
    <kwd>asymmetrical dinitrobenzophenones</kwd>
    <kwd>nitro group</kwd>
    <kwd>nitroamines</kwd>
   </kwd-group>
  </article-meta>
 </front>
 <body>
  <p></p>
 </body>
 <back>
  <ref-list>
   <ref id="B1">
    <label>1.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Pinheiro, H.M., Touraud, E. &amp; Thomas, O. (2004) Aromatic amines from azo dye reduction: status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters, Dyes Pigm, (61), pp. 121−139. DOI: 10.1016/j.dyepig.2003.10.009.</mixed-citation>
     <mixed-citation xml:lang="en">Pinheiro, H.M., Touraud, E. &amp; Thomas, O. (2004) Aromatic amines from azo dye reduction: status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters, Dyes Pigm, (61), pp. 121−139. DOI: 10.1016/j.dyepig.2003.10.009.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B2">
    <label>2.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Bindra, A.P. (2006) Heat stable laked monoazo red pigment. 1668081 EP.</mixed-citation>
     <mixed-citation xml:lang="en">Bindra, A.P. (2006) Heat stable laked monoazo red pigment. 1668081 EP.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B3">
    <label>3.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Waware, U.S., Hamouda, A.M.S. &amp; Majumdar, D. (2019) Synthesis, characterization and physicochemical studies of copolymers of aniline and 3-nitroaniline, Polymer Bulletin, 77(9), pp. 4469–4488. DOI: 10.1007/s00289-019-02957-y.</mixed-citation>
     <mixed-citation xml:lang="en">Waware, U.S., Hamouda, A.M.S. &amp; Majumdar, D. (2019) Synthesis, characterization and physicochemical studies of copolymers of aniline and 3-nitroaniline, Polymer Bulletin, 77(9), pp. 4469–4488. DOI: 10.1007/s00289-019-02957-y.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B4">
    <label>4.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Selvaraj. P., Subramani, K., Srinivasan. B., Hsu, C.-J. &amp; Huang, C.-Y. (2020) Electro-optical effects of organic N-benzyl-2-methyl-4-nitroaniline dispersion in nematic liquid crystals, Scientific Reports, 10(1). DOI: 10.1038/s41598-020-71306-1.</mixed-citation>
     <mixed-citation xml:lang="en">Selvaraj. P., Subramani, K., Srinivasan. B., Hsu, C.-J. &amp; Huang, C.-Y. (2020) Electro-optical effects of organic N-benzyl-2-methyl-4-nitroaniline dispersion in nematic liquid crystals, Scientific Reports, 10(1). DOI: 10.1038/s41598-020-71306-1.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B5">
    <label>5.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Conoci, S., Petralia, S. &amp; Sortino, S. (2013) Use of nitroaniline derivatives for the production of nitric oxide. 8440849 US.</mixed-citation>
     <mixed-citation xml:lang="en">Conoci, S., Petralia, S. &amp; Sortino, S. (2013) Use of nitroaniline derivatives for the production of nitric oxide. 8440849 US.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B6">
    <label>6.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Smirnov, S.P., Feshchenko, A.G. &amp; Kiseleva, A.S. (2016) Method for the preparation of 5-amino-4,6-dinitrobenzofuroxane. 1841243 RU (in Russian).</mixed-citation>
     <mixed-citation xml:lang="en">Smirnov, S.P., Feshchenko, A.G. &amp; Kiseleva, A.S. (2016) Method for the preparation of 5-amino-4,6-dinitrobenzofuroxane. 1841243 RU (in Russian).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B7">
    <label>7.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Wei, H.Y., Xu, C.H., &amp; Zhou, P.H. (2018) Method for synthesizing intermediate of Bendamustine hydrochloride. 108358848 CN.</mixed-citation>
     <mixed-citation xml:lang="en">Wei, H.Y., Xu, C.H., &amp; Zhou, P.H. (2018) Method for synthesizing intermediate of Bendamustine hydrochloride. 108358848 CN.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B8">
    <label>8.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Porter, H.K. (1973) The Zinin Reduction of Nitroarenes, Organic Reactions, 20(4), pp. 455-481 [online]. Available at: https://doi.org/10.1002/0471264180.or020.04</mixed-citation>
     <mixed-citation xml:lang="en">Porter, H.K. (1973) The Zinin Reduction of Nitroarenes, Organic Reactions, 20(4), pp. 455-481 [online]. Available at: https://doi.org/10.1002/0471264180.or020.04</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B9">
    <label>9.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Hou. J., Ma, Y., Li, Y., Guo, F. &amp; Lu, L. (2008) Selective Partial Hydrogenation of Dinitrobenzenes to Nitroanilines Catalyzed by Ru/C, Chemistry Letters, 37(9), pp. 974-975. DOI: 10.1246/cl.2008.974.</mixed-citation>
     <mixed-citation xml:lang="en">Hou. J., Ma, Y., Li, Y., Guo, F. &amp; Lu, L. (2008) Selective Partial Hydrogenation of Dinitrobenzenes to Nitroanilines Catalyzed by Ru/C, Chemistry Letters, 37(9), pp. 974-975. DOI: 10.1246/cl.2008.974.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B10">
    <label>10.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Grieco, G. &amp; Blacque, O. (2021) Microwave-assisted reduction of aromatic nitro compounds with novel oxo-rhenium complexes, Applied Organometallic Chemistry, 36(1), e6452. DOI: 10.1002/aoc.6452.</mixed-citation>
     <mixed-citation xml:lang="en">Grieco, G. &amp; Blacque, O. (2021) Microwave-assisted reduction of aromatic nitro compounds with novel oxo-rhenium complexes, Applied Organometallic Chemistry, 36(1), e6452. DOI: 10.1002/aoc.6452.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B11">
    <label>11.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Romero, A. &amp; Cerecetto, H. (2020) A common, facile and eco-friendly method for the reduction of ni-troarenes, selective reduction of polynitroarenes and deoxygenation of N-oxide containing heteroarenes, Eu-ropean Journal of Organic Chemistry, 2020(12), pp. 1853-1865. DOI: 10.1002/ejoc.202000064.</mixed-citation>
     <mixed-citation xml:lang="en">Romero, A. &amp; Cerecetto, H. (2020) A common, facile and eco-friendly method for the reduction of ni-troarenes, selective reduction of polynitroarenes and deoxygenation of N-oxide containing heteroarenes, Eu-ropean Journal of Organic Chemistry, 2020(12), pp. 1853-1865. DOI: 10.1002/ejoc.202000064.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B12">
    <label>12.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Theodoridis, G., Manfredi, M.C. &amp; Krebs, J.D. (1990) Selective hydrogenation of polynitroaromatic derivatives with noble metal catalysts in the presence of catalytic amounts of iron, Tetrahedron Letters, 31(43), pp. 6141–6144. DOI: 10.1016/s0040-4039(00)97008-4.</mixed-citation>
     <mixed-citation xml:lang="en">Theodoridis, G., Manfredi, M.C. &amp; Krebs, J.D. (1990) Selective hydrogenation of polynitroaromatic derivatives with noble metal catalysts in the presence of catalytic amounts of iron, Tetrahedron Letters, 31(43), pp. 6141–6144. DOI: 10.1016/s0040-4039(00)97008-4.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B13">
    <label>13.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Terpko, M.O. &amp; Heck, R.F. (1980) Palladium-catalyzed triethylammonium formate reductions. 3. Selective reduction of dinitroaromatic compounds, The Journal of Organic Chemistry, 45(24), pp. 4992-4993. DOI: 10.1021/jo01312a039.</mixed-citation>
     <mixed-citation xml:lang="en">Terpko, M.O. &amp; Heck, R.F. (1980) Palladium-catalyzed triethylammonium formate reductions. 3. Selective reduction of dinitroaromatic compounds, The Journal of Organic Chemistry, 45(24), pp. 4992-4993. DOI: 10.1021/jo01312a039.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B14">
    <label>14.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Begunov, R.S. &amp; Sokolov, A.A. (2022) One-reactor reduction and halogenation of n-(2,4-dinitrophenyl)piperidine, From Chemistry Towards Technology Step-By-Step, 3(2), pp. 30-36. DOI: 10.52957/27821900_2022_02_30. 481 [online]. Available at: chemintech.ru/index.php/tor/2022tom3no2 (in Russian).</mixed-citation>
     <mixed-citation xml:lang="en">Begunov, R.S. &amp; Sokolov, A.A. (2022) One-reactor reduction and halogenation of n-(2,4-dinitrophenyl)piperidine, From Chemistry Towards Technology Step-By-Step, 3(2), pp. 30-36. DOI: 10.52957/27821900_2022_02_30. 481 [online]. Available at: chemintech.ru/index.php/tor/2022tom3no2 (in Russian).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B15">
    <label>15.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Liu, S.S., Liu, X., Yu, L., Liu, Y.M., He, H.Y. &amp; Cao, Y. (2014) Gold supported on titania for specific monohy-drogenation of dinitroaromatics in the liquid phase, Green Chemistry, 16(9), pp. 4162−4169. DOI: 10.1039/c4gc00869c.</mixed-citation>
     <mixed-citation xml:lang="en">Liu, S.S., Liu, X., Yu, L., Liu, Y.M., He, H.Y. &amp; Cao, Y. (2014) Gold supported on titania for specific monohy-drogenation of dinitroaromatics in the liquid phase, Green Chemistry, 16(9), pp. 4162−4169. DOI: 10.1039/c4gc00869c.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B16">
    <label>16.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Guillén, E., Rico, R., López-Romero, J.M., Bedia, J., Rosas, J.M., Rodríguez-Mirasol, J. &amp; Cordero, T. (2009) Pd-activated carbon catalysts for hydrogenation and Suzuki reactions, Applied Catalysis A: General, 368(1-2), pp. 113–120. DOI: 10.1016/j.apcata.2009.08.016.</mixed-citation>
     <mixed-citation xml:lang="en">Guillén, E., Rico, R., López-Romero, J.M., Bedia, J., Rosas, J.M., Rodríguez-Mirasol, J. &amp; Cordero, T. (2009) Pd-activated carbon catalysts for hydrogenation and Suzuki reactions, Applied Catalysis A: General, 368(1-2), pp. 113–120. DOI: 10.1016/j.apcata.2009.08.016.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B17">
    <label>17.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Yuan, M., Long, Y., Yang, J., Hu, X., Xu, D., Zhu, Y. &amp; Dong, Z. (2018) Biomass sucrose derived co-balt@nitrogen-doped carbon for catalytic transfer hydrogenation of nitroarenes with formic acid, ChemSus-Chem, 11(23), pp. 4156-4165. DOI: 10.1002/cssc.201802163.</mixed-citation>
     <mixed-citation xml:lang="en">Yuan, M., Long, Y., Yang, J., Hu, X., Xu, D., Zhu, Y. &amp; Dong, Z. (2018) Biomass sucrose derived co-balt@nitrogen-doped carbon for catalytic transfer hydrogenation of nitroarenes with formic acid, ChemSus-Chem, 11(23), pp. 4156-4165. DOI: 10.1002/cssc.201802163.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B18">
    <label>18.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Leibzon, V.N., Michalchenko, L.V., Leonova, M.Y. &amp; Gultyai V.P. (2005) Change in Regioselectivity in the Monoreduction of 2,4,6-Trinitrotoluene with Titanium(III) and Vanadium(II) Ions in the Presence of Iron(II) and Copper(II) Salts, Russian Chemical Bulletin, 54(5), pp. 1203-1207. DOI: 10.1002/chin.200629061.</mixed-citation>
     <mixed-citation xml:lang="en">Leibzon, V.N., Michalchenko, L.V., Leonova, M.Y. &amp; Gultyai V.P. (2005) Change in Regioselectivity in the Monoreduction of 2,4,6-Trinitrotoluene with Titanium(III) and Vanadium(II) Ions in the Presence of Iron(II) and Copper(II) Salts, Russian Chemical Bulletin, 54(5), pp. 1203-1207. DOI: 10.1002/chin.200629061.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B19">
    <label>19.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">McHugh, C.J., Keir, R., Graham, D. &amp; Smith, W.E. (2002) Selective functionalisation of TNT for sensitive de-tection by SERRS, Chemical Communications, (6), pp. 580–581. DOI: 10.1039/b110972c.</mixed-citation>
     <mixed-citation xml:lang="en">McHugh, C.J., Keir, R., Graham, D. &amp; Smith, W.E. (2002) Selective functionalisation of TNT for sensitive de-tection by SERRS, Chemical Communications, (6), pp. 580–581. DOI: 10.1039/b110972c.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B20">
    <label>20.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Bellamy. F.D. &amp; Ou, K. (1984) Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium, Tetrahedron Letters, 25(8), pp. 839–842. DOI: 10.1016/s0040-4039(01)80041-1.</mixed-citation>
     <mixed-citation xml:lang="en">Bellamy. F.D. &amp; Ou, K. (1984) Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium, Tetrahedron Letters, 25(8), pp. 839–842. DOI: 10.1016/s0040-4039(01)80041-1.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B21">
    <label>21.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Bilkis, I.I., Uskov, S.I., Galdilov, V.S. &amp; Steingartz, V.D. (1986) Anion radicals of aromatic compounds. IX. Peculiarities of electronic structure of radical anion 1-substituted 2,4-dinitrobenzenes in aqueous and aqueous-alcoholic media, Zhurnal organicheskoj himii, 22(6), pp. 1247-1254 (in Russian).</mixed-citation>
     <mixed-citation xml:lang="en">Bilkis, I.I., Uskov, S.I., Galdilov, V.S. &amp; Steingartz, V.D. (1986) Anion radicals of aromatic compounds. IX. Peculiarities of electronic structure of radical anion 1-substituted 2,4-dinitrobenzenes in aqueous and aqueous-alcoholic media, Zhurnal organicheskoj himii, 22(6), pp. 1247-1254 (in Russian).</mixed-citation>
    </citation-alternatives>
   </ref>
  </ref-list>
 </back>
</article>
