vuzbiochemiИзвестия вузов. Прикладная химия и биотехнологияProceedings of Universities. Applied Chemistry and Biotechnology2227-29252500-1558ИРНИТУ10.21285/2227-2925-2019-9-4-576-589vuzbiochemi-253Research ArticleХИМИЧЕСКИЕ НАУКИCHEMICAL SCIENCESХалькогенирование ненасыщенных галогенорганических соединений элементными халькогенами и их металлическими производнымиChalcogenisation of unsaturated organohalogen compounds by elemental chalcogens and their metal derivativesРозенцвейгИ. Б.RozentsveigI. B.

Розенцвейг Игорь Борисович, д.х.н., доцент, заведующий лабораторией галогенорганических соединений

664033, г. Иркутск, ул. Фаворского, 1

профессор кафедры теоретической и прикладной органической химии и полимеризационных процессов

664003, ул. К. Маркса, 1

Igor B. Rozentsveig, Dr. Sci. (Chemistry), Associated Professor, Head of Laboratory of Haloorganic Compounds

1, Favorsky St., Irkutsk, 664033

Professor, Department of Theoretical and Applied Organic Chemistry and Polymerization Processes

1, K. Marks St., Irkutsk, 664003

i_roz@irioch.irk.ruНиконоваВ. С.NikonovaV. S.

Никонова Валентина Сергеевна, к.х.н., научный сотрудник

664033, г. Иркутск, ул. Фаворского, 1

Valentina S. Nikonova, Cand. Sci. (Chemistry), Reseacher

1, Favorsky St., Irkutsk, 664033

valentina_serg@inbox.ruКорчевинН. А.KorchevinN. A.

Корчевин Николай Алексеевич, д.х.н., профессор, ведущий научный сотрудник

664033, г. Иркутск, ул. Фаворского, 1

профессор кафедры технологии электрохимических производств

665835, г. Ангарск, ул. Чайковского, 60

Nikolai A. Korchevin, Dr. Sci. (Chemistry), Professor, Leading Researcher

1, Favorsky St., Irkutsk 664033

Professor, Department of Electrochemical Production Technologies

60, Chaikovsky St., Angarsk 665835

rusnatali64@yandex.ruИркутский институт химии им. А.Е. Фаворского СО РАН, Иркутский государственный университетРоссияA.E. Favorsky Irkutsk Institute of Chemistry SB RAS; Irkutsk State UniversityRussian FederationИркутский институт химии им. А.Е. Фаворского СО РАН,РоссияA.E. Favorsky Irkutsk Institute of Chemistry SB RASRussian FederationИркутский институт химии им. А.Е. Фаворского СО РАН, Ангарский государственный технический университетРоссияA.E. Favorsky Irkutsk Institute of Chemistry SB RAS; Angarsk State Technical UniversityRussian Federation20190501202094576589Copyright © Розенцвейг И.Б., Никонова В.С., Корчевин Н.А., 20202020Розенцвейг И.Б., Никонова В.С., Корчевин Н.А.Rozentsveig I.B., Nikonova V.S., Korchevin N.A.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vuzbiochemi.elpub.ru/jour/article/view/253

В представленном обзоре рассмотрены вопросы, касающиеся перспектив использования халькогенорганических соединений в медицине, сельском хозяйстве, в различных областях техники и в органическом синтезе. Показано, что ненасыщенные продукты халькогенирования представляют гораздо больший интерес по сравнению с их насыщенными аналогами, особенно при использовании в органическом синтезе. В качестве ненасыщенных субстратов, подвергаемых халькогенированию, представлены галогенпроизводные этена, пропена, пропина и бутена. Указанные реагенты относятся либо к многотоннажным продуктам промышленного хлорорганического синтеза, либо являются отходами хлорорганических производств, утилизация которых является важной экологической задачей. Проанализированные публикации отражают процессы халькогенирования, базирующиеся на использовании элементных халькогенов (серы, селена и теллура) или их доступных металлических производных (Na2S и др.). Для осуществления реакций халькогенов с ненасыщенными галогенпроизводными элементы в доступной форме в свободном состоянии подвергают восстановительной активации, в результате которой образуются анионные нуклеофильные реагенты. В качестве восстановителей показаны примеры использования комплексных гидридов металлов, халькогениданионов и ронгалита. В обзоре подчеркнуты перспективы применения для целей активации основно-восстановительных систем на базе гидразингидрата. Показаны особенности введения в качестве оснований в эти системы едких щелочей и органического амина – моноэтаноламина. Для рассмотренных процессов халькогенирования указаны условия, обеспечивающие наиболее оптимальные выходы определенных продуктов. В необходимых случаях представлена стереохимия получаемых соединений и рассмотрены условия образования стереоизомеров определенной конфигурации. Для некоторых получаемых соединений показаны перспективы практического применения. Материал обзора будет полезен специалистам в области органического синтеза и практического использования халькогенорганических соединений.

Авторы заявляют об отсутствии конфликта интересов.

The presented review addresses the prospects for application of organochalcogen compounds in various fields of technology, medicine, agriculture and organic synthesis. The unsaturated chalcogenisation products appear to be of much greater interest compared to their saturated analogues, especially in organic synthesis. This study observes halogen derivatives of ethene, propene, propyne and butene subjected to chalcogenisation as unsaturated substrates. The indicated reagents are related either to large-tonnage products of industrial organochlorine synthesis or waste products of organochlorine production with their disposal presenting an important environmental task. According to analysed publications, chalcogenisation processes are based on the application of elemental chalcogens (sulphur, selenium, and tellurium) or their available metal derivatives (Na2S, etc.). In the reactions of chalcogens with unsaturated halogen derivatives, the elements both in an accessible form and in a free state are subjected to reductive activation resulting in the formation of anionic nucleophilic reagents. Complex metal hydrides, chalcogenide anions and rongalite are exampled for application in terms of reducing agents. The review emphasises the prospects of basic reduction systems based on hydrazine hydrate in activation processes. Special aspects in the introduction of caustic alkalis and an monoethanolamine organic amine as bases in these systems are described. For the considered chalcogenisation processes, conditions are specified providing the most optimal yield of certain products. In some particular cases, the stereochemistry of the obtained compounds is presented considering the formation conditions for the stereoisomers of a certain configuration. For a number of the obtained compounds, the prospects of practical application are provided. In general, the current review is intended for specialists working in the field of organic synthesis and application of organochalcogen compounds.

The authors declare no conflict of interests regarding the publication of this article.

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