Details

Autor(en) / Beteiligte

• Baroudi, Abdulkader
• Flack, Phillip
• Alabugin, Igor V.

Titel

Metal-Free Transformation of Phenols into Substituted Benzamides: A Highly Selective Radical 1,2-O→C Transposition in O-Aryl-N-phenylthiocarbamates

Ist Teil von

• Chemistry : a European journal, 2010-11, Vol.16 (41), p.12316-12320

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2010

Quelle

Wiley Online Library - AutoHoldings Journals

Beschreibungen/Notizen

• Radical merry‐go‐round: A highly efficient metal‐free transformation of phenols into benzamides is designed through one‐step conversion of phenols to aryl thiocarbamates and a subsequent radical addition/rearrangement/fragmentation cascade. Computational analysis fully rationalizes the experimentally observed selectivity. Despite the possible competition from NC fragmentation and N‐neophyl rearrangement, the transformation exclusively follows the most kinetically and thermodynamically favored O‐neophyl rearrangement path.