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Self‐Terminating Radical Oxygenations: Probing of the Scope of the Concept by Use of Various Organic O ‐Centered Radicals
Author(s) -
Jargstorff Christian,
Wille Uta
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300257
Subject(s) - chemistry , radical , stereochemistry , polymer chemistry , photochemistry , organic chemistry , medicinal chemistry
Addition of various organic O ‐centered radicals XO • {i.e. (alkoxycarbonyl)oxyl radicals, ROC(O)O • , [(alkoxycarbonyl)acyl]oxyl radicals, ROC(O)C(O)O • , (carbamoyl)oxyl radicals, R 2 NC(O)O • , alkoxyl radicals, RO • , and nitroxyl radicals, R 2 NO • } to alkynes initiates an oxidative radical cyclization cascade, which is terminated by release of a C ‐ or N ‐centered radical X • . This finding clearly highlights the generality of the recently discovered concept of self‐terminating radical oxygenations, through which C≡C triple bonds may be converted into carbonyl groups under very mild reaction conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)