Halogenated Donor-Acceptor Cyclopropanes as Donor-Acceptor Cyclopropene Surrogates
Gwyndaf A Oliver1, Simon Kolb1, Malini George1
1Albert-Ludwigs-Universität Freiburg, Institute of Organic Chemistry, Albertstr. 21, 79104, Freiburg (im Breisgau), Germany.
Abstract:
Herein we report (3+2)-cycloaddition reactions of halogenated donor-acceptor cyclopropanes (HDACs) as surrogates for donor-acceptor cyclopropenes. Upon reaction with a variety of 2π-components, cycloaddition followed by elimination generates the unsaturated five-membered ring products. A series of HDACs were shown to be effective in reactions with thioketones. Five further cycloaddition reactions were used to showcase the broad applicability of these donor-acceptor cyclopropene surrogates. Kinetic studies allowed the proposal of a plausible mechanism for this reaction.
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