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Stability and Cyclization of Enol Radical Cations: A Mechanistic Study of One‐Electron Oxidation of β,β‐Dimesityl Enols
Author(s) -
Schmittel Michael,
Baumann Ulrich
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199005411
Subject(s) - enol , yield (engineering) , chemistry , medicinal chemistry , photochemistry , radical ion , computational chemistry , organic chemistry , catalysis , thermodynamics , ion , physics
A reversal in the position of the keto/enol equilibrium through one‐electron oxidationa —a phenomenon already observed in the gas phase—has now also been verified in solution. The Δ G ° values ( 1 ˙⊕ → 2 ˙⊕ ) for the two enols 1 (R = t Bu, H) are −17.7 and −25.7 kcal mol −1 . Benzofurans 2 are obtained as reaction products from the radical cations in over 80% yield.