[4+3] Cycloaddition of Donor–Acceptor Cyclopropanes with Amphiphilic Benzodithioloimine as Surrogate for ortho‐Bisthioquinone |
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Authors: | Lennart K B Garve Dr Martin Pawliczek Jan Wallbaum Prof?Dr Peter G Jones Prof?Dr Daniel B Werz |
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Institution: | 1. Technische Universit?t Braunschweig, Institute of Organic Chemistry, Hagenring?30, 38106 Braunschweig (Germany) http://www.werzlab.de;2. Technische Universit?t Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring?30, 38106 Braunschweig (Germany) |
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Abstract: | Donor–acceptor cyclopropanes were reacted with amphiphilic benzodithioloimine to give seven‐membered heterocycles with two sulfur atoms. Formally, this transformation can be regarded as a 4+3] cycloaddition reaction of the three‐membered ring and ortho‐bisthioquinone. The benzodithioloimine serves as a surrogate for this highly reactive diene. The structure of the products was confirmed by X‐ray crystallography. Broad signals in 13C NMR studies suggest that several conformers, slowly interconverting on the NMR timescale, are present at room temperature. |
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Keywords: | cycloaddition cyclopropanes heterocycles Lewis acids |
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