Content:
Chapter 12 Syntheses and makes use of of isotopically labelled quinones (pages 617–682): Mieczyslaw Zielinski
Chapter thirteen organic reactions of qyinones (pages 683–736): Ronald Bentley and Iain M. Campbell
Chapter 14 Electrochemistry of quinones (pages 737–791): James Q. Chambers
Chapter 15 Polymeric quinones (pages 793–855): A. S. Lindsey
Chapter sixteen Non?benzenoid quinones (pages 857–875): T. A. Turney
Chapter 17 The addition and substitution chemistry of quinones (pages 877–1144): okay. Thomas Finley
Chapter 18 Quinone methides (pages 1145–1178): H.?U. Wagner and R. Gompper
Read or Download Quinonoid Compounds: Volume 2 (1974) PDF
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Additional info for Quinonoid Compounds: Volume 2 (1974)
Sample text
This has been carried out according to scheme (94). Radioactive bromine was added to nienadione in the presence of sodiuni acetate and acetic acid at liquid air temperature. The contents were warmed to 50°C in a water bath and further acetic acid was added. After 3 h water was added to precipitate the labelled quinone 113. KB2h MnO,, H S O , ' rnenadione 82 Br2 CH,COONa CH,COOH & -HBr ~ H Br \ 0 (941 12. Syntheses and uses of isotopically labelled quinones 659 111. TRACER APPLICATIONS O F LABELLED QUINONES A.
3= - ‘‘0 i’‘OH? (86) The isotope equilibrium was reached after 10 days in neutral medium. r. r. spcctroscopy, and also on 1 7 0 and I s 0 applications in physical and life sciences, in the catalogue of I*O- and 170-labclled compounds edited by the Research Products Dept. A. r. spectra of deutcrated and 190-labelled quinones are reviewed in the hook of S . Pinchas and I . Laulicht, lifinred Sprctrn of Labe“ed Coniponnds, Academic PI-css, London and New York, 1971. 12. Syntheses and uses of isotopically labelled quinones 653 The isotope exchange reaction (86) can be used for synthesis of lSO labelled quinones.
The Frics rearrangementlo* of 58 gave 2-bromo-4’-hydroxybenzophenone (59) which was reduced to 2-bromo-4‘-hydroxydiphenylmethane(60). The hydroxyl group is protected in the next stcp by formation of a cyclic acetal with dihydropyranllO. The halogen-metal interconversion with 61 and butyllithium yields the organolithiuni compound 62, which was carbonated with labelled carbon dioxide. Ring closure of 63 gave 2-hydroxy-9anthrone (64) in 88-1 00% yield”’, which was oxidized to 2-hydroxyanthraquinone (65) in practically quantitative yield.