Svjetlom do heteropolicikličkih spojeva; Reakcije supstituiranih furostilbena
Synthetic organic photochemistry, the chemistry of excited states of a molecule, differs from the ground state chemistry and provides a simple pathway to complicated structures, heavily obtainable by a classic synthetic approach. In this paper the polycyclic structures with oxygen, prepared by photo...
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| Format: | Article |
| Language: | English |
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Croatian Society of Chemical Engineers
2007-03-01
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| Series: | Kemija u Industriji |
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| Online Access: | http://pierre.fkit.hr/hdki/kui/vol56/broj03/135.pdf |
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| author | Šindler-Kulyk, M. Škorić, I. |
| author_facet | Šindler-Kulyk, M. Škorić, I. |
| author_sort | Šindler-Kulyk, M. |
| collection | DOAJ |
| description | Synthetic organic photochemistry, the chemistry of excited states of a molecule, differs from the ground state chemistry and provides a simple pathway to complicated structures, heavily obtainable by a classic synthetic approach. In this paper the polycyclic structures with oxygen, prepared by photochemical methodology of new o-substituted furan heterostilbenes are reviewed. The photochemistry of β-(2-furyl)-substituted-o-divinylbenzenes <b>6,13,15</b>, β,β-di(2-furyl)-substituted o-divinylbenzenes <b>18-20</b>, aryl and heteroaryl analogues of 2,3-distyrylfurans 33-36 is described. Due to steric reasons, on irradiation of β-(3-substituted-2-furyl)-o-divinylbenzenes 6, the preferred photoreaction was the intramolecular [2+2]-cycloaddition and formation of the bicyclo[2.1.1]hexenes <b>10</b> along with the formation of the corresponding phenanthrenes 12. On the other hand, furan analogues 6 and 13 give bicyclo[3.2.1]octadiene structures in very good yield. Di-substituted o-divinylbenzene derivatives <b>18-20</b> (with a hexatriene system as part of the aromatic ring) give bicyclo[3.2.1]octadiene derivatives <b>21-23</b> by intramolecular photocycloaddition and cyclophane derivatives <b>24-26</b> by intermolecular [2+2] two-fold photoaddition reaction. Compound 20 is the most selective of these o-divinylbenzenes yielding only the exo-bicyclo[3.2.1]octadiene derivative <b>23</b> at low concentrations, and only the cyclophane derivative 26 at high concentrations. This reaction to <b>23</b> and <b>26</b> is due - intra- or intermolecular complexation. Contrary to these results, on the irradiation of the aryl and heteroaryl analogues of 2,3-distyrylfurans <b>33-36</b> (with a hexatriene system as part of the heteroaromatic ring) different intra- and intermolecular processes have been observed. By intramolecular [2+2]-cycloaddition, this hexatriene system gives the phototransposition products. Also observed are stilbenes and phenanthrenes as secondary products obtained from the primary formed intermolecular cyclobutane adducts. |
| first_indexed | 2024-04-12T16:41:16Z |
| format | Article |
| id | doaj.art-414a8c049eb043adbf198548bc61f672 |
| institution | Directory Open Access Journal |
| issn | 0022-9830 1334-9090 |
| language | English |
| last_indexed | 2024-04-12T16:41:16Z |
| publishDate | 2007-03-01 |
| publisher | Croatian Society of Chemical Engineers |
| record_format | Article |
| series | Kemija u Industriji |
| spelling | doaj.art-414a8c049eb043adbf198548bc61f6722022-12-22T03:24:47ZengCroatian Society of Chemical EngineersKemija u Industriji0022-98301334-90902007-03-015603135143Svjetlom do heteropolicikličkih spojeva; Reakcije supstituiranih furostilbenaŠindler-Kulyk, M.Škorić, I.Synthetic organic photochemistry, the chemistry of excited states of a molecule, differs from the ground state chemistry and provides a simple pathway to complicated structures, heavily obtainable by a classic synthetic approach. In this paper the polycyclic structures with oxygen, prepared by photochemical methodology of new o-substituted furan heterostilbenes are reviewed. The photochemistry of β-(2-furyl)-substituted-o-divinylbenzenes <b>6,13,15</b>, β,β-di(2-furyl)-substituted o-divinylbenzenes <b>18-20</b>, aryl and heteroaryl analogues of 2,3-distyrylfurans 33-36 is described. Due to steric reasons, on irradiation of β-(3-substituted-2-furyl)-o-divinylbenzenes 6, the preferred photoreaction was the intramolecular [2+2]-cycloaddition and formation of the bicyclo[2.1.1]hexenes <b>10</b> along with the formation of the corresponding phenanthrenes 12. On the other hand, furan analogues 6 and 13 give bicyclo[3.2.1]octadiene structures in very good yield. Di-substituted o-divinylbenzene derivatives <b>18-20</b> (with a hexatriene system as part of the aromatic ring) give bicyclo[3.2.1]octadiene derivatives <b>21-23</b> by intramolecular photocycloaddition and cyclophane derivatives <b>24-26</b> by intermolecular [2+2] two-fold photoaddition reaction. Compound 20 is the most selective of these o-divinylbenzenes yielding only the exo-bicyclo[3.2.1]octadiene derivative <b>23</b> at low concentrations, and only the cyclophane derivative 26 at high concentrations. This reaction to <b>23</b> and <b>26</b> is due - intra- or intermolecular complexation. Contrary to these results, on the irradiation of the aryl and heteroaryl analogues of 2,3-distyrylfurans <b>33-36</b> (with a hexatriene system as part of the heteroaromatic ring) different intra- and intermolecular processes have been observed. By intramolecular [2+2]-cycloaddition, this hexatriene system gives the phototransposition products. Also observed are stilbenes and phenanthrenes as secondary products obtained from the primary formed intermolecular cyclobutane adducts.http://pierre.fkit.hr/hdki/kui/vol56/broj03/135.pdfphotochemistryfuranhetero-polycyclic compounds |
| spellingShingle | Šindler-Kulyk, M. Škorić, I. Svjetlom do heteropolicikličkih spojeva; Reakcije supstituiranih furostilbena Kemija u Industriji photochemistry furan hetero-polycyclic compounds |
| title | Svjetlom do heteropolicikličkih spojeva; Reakcije supstituiranih furostilbena |
| title_full | Svjetlom do heteropolicikličkih spojeva; Reakcije supstituiranih furostilbena |
| title_fullStr | Svjetlom do heteropolicikličkih spojeva; Reakcije supstituiranih furostilbena |
| title_full_unstemmed | Svjetlom do heteropolicikličkih spojeva; Reakcije supstituiranih furostilbena |
| title_short | Svjetlom do heteropolicikličkih spojeva; Reakcije supstituiranih furostilbena |
| title_sort | svjetlom do heteropoliciklickih spojeva reakcije supstituiranih furostilbena |
| topic | photochemistry furan hetero-polycyclic compounds |
| url | http://pierre.fkit.hr/hdki/kui/vol56/broj03/135.pdf |
| work_keys_str_mv | AT sindlerkulykm svjetlomdoheteropoliciklickihspojevareakcijesupstituiranihfurostilbena AT skorici svjetlomdoheteropoliciklickihspojevareakcijesupstituiranihfurostilbena |