Radical oxygenations with inorganic radicals: can hydroxyl radicals (HO) act as donors of oxygen atoms?
Hydroxyl radicals (HO) were shown to act, upon addition to the CC triple bond in cyclic and open-chain alkynes, as oxygen atom donors in an oxidative radical cyclization sequence.
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Acknowledgments
This work was in part supported by the Fonds der Chemischen Industrie and the Dr. Otto Röhm-Gedächtnisstiftung. I thank Christian Jargstorff for the synthesis of compound 9.
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2010, TetrahedronCitation Excerpt :In each of these examples there is no possibility of regioisomers being formed and the yields of the germanium-mediated cyclisations are considerably higher than those observed in Scheme 60. Cyclisation on to pyrroles can suffer from regiochemistry issues (Scheme 61).133 In the reactions of amides 209 the regiochemistry is governed by the substituent on the pyrrole nitrogen; unsubstituted pyrroles (R3=H) gave a 2:1 mixture of pyrroloquinolines 210 and 211 formed by a 6-endo-trig or 6-exo-trig cyclisation followed by re-aromatisation.
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