Preparation and reactivity of macrocyclic dienynes |
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Authors: | Herbert Meier Hans-Joachim Bissinger Anita Vierengel |
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Institution: | Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, 55099 Mainz, Germany |
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Abstract: | (1E,5E)-Cyclopentadeca-1,5-dien-3-yne (1c), which represents the first macrocyclic 1,5-dien-3-yne, can be obtained by thermal- or butyllithium-induced fragmentation of the corresponding 1,2,3-selenadiazole 8. The (E,E)-dienyne functionality causes a geometrical strain Eg, which enhances the reactivity in addition (1c→12,13) and cycloaddition (1c→10) reactions and lowers the isomerization barrier to the unstrained (E,Z)-configuration 1d (Eg = 0). A slow process 1c→1d occurs even at ambient temperatures within several weeks. |
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