The phototransposition reactions of thiophene- carbonitriles were shown to occur via the intermediate formation and isomerisation of 5-thiabicyclo[2˙1˙0]pent- 2-enes . Thus, irradiation of thiophene-3-carbonitrile in cyclohexane gave 5-thiabieyelo[2˙1˙0]pent-2-ene-2-carbonitrile as the primary photochemical product. Further irradiation produced thiophene-2-carbonitrile. The reaction was reversible, Addition of furan to 5-thiabicyclo[2˙1˙0]pent-2-ene-2- carbonitrile yielded a mixture of exo and endo-10,4-oxa thiatetracyclo[5˙2˙1˙0,sup>2,6</sup>˙ 0sup>3,5</sup>]dec-8-ene-2-carbonitrile. These two adducts were similarly formed upon irradiation of either thiophene-2 or 3-carbonitrile in furan.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:460420 |
| Date | January 1978 |
| Creators | Irving, Edward |
| Contributors | Day, A. C. |
| Publisher | University of Oxford |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://ora.ox.ac.uk/objects/uuid:a4b85054-657e-42d9-ba82-b6cc80818722 |
Page generated in 0.0015 seconds