Elsevier

Tetrahedron Letters

Volume 43, Issue 7, 11 February 2002, Pages 1239-1242
Tetrahedron Letters

Radical oxygenations with inorganic radicals: can hydroxyl radicals (HOradical dot) act as donors of oxygen atoms?

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Abstract

Hydroxyl radicals (HOradical dot) were shown to act, upon addition to the Csingle bondC triple bond in cyclic and open-chain alkynes, as oxygen atom donors in an oxidative radical cyclization sequence.

Hydroxyl radicals (HOradical dot) were shown to act, upon addition to the Csingle bondC 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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  • Radicals in organic synthesis: part 2

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    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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