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Attempts to construct fused 7,7-bicyclic compounds from acyclic dienynes by tandem RCM failed (see ref. 7e).
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Attempts to construct fused 7,7-bicyclic compounds from acyclic dienynes by tandem RCM failed (see ref. 7e).
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23
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34250802975
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6-Bromo-2-methyl-hex-2-ene was prepared in three steps from y-butyrolactone: reduction with DIBAH followed by Wittig reaction and bromation of the resulting primary alcohol. For details see Supporting Information.
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6-Bromo-2-methyl-hex-2-ene was prepared in three steps from y-butyrolactone: reduction with DIBAH followed by Wittig reaction and bromation of the resulting primary alcohol. For details see Supporting Information.
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24
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34250847380
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To get the indicated yield, it is important to observe the following work up. After the completion of the reaction, silica gel was added at -70 °C, and the reaction mixture was allowed to warm to 0°C. The crude aldehyde was isolated by filtration and was purified by flash column chromatography. Otherwise, treatment of the reaction mixture with Rochelle's salt (potassium and sodium tartrate solution) resulted in the complete degradation of the product.
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To get the indicated yield, it is important to observe the following work up. After the completion of the reaction, silica gel was added at -70 °C, and the reaction mixture was allowed to warm to 0°C. The crude aldehyde was isolated by filtration and was purified by flash column chromatography. Otherwise, treatment of the reaction mixture with Rochelle's salt (potassium and sodium tartrate solution) resulted in the complete degradation of the product.
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Wenkert, E.; Kim, H.-S. In Studies in Natural Products Chemistry; Atta-ur-Rhaman, Ed.; Elsevier: Amsterdam, The Netherlands, 1989; 3, Part B, p 287.
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Wenkert, E.; Kim, H.-S. In Studies in Natural Products Chemistry; Atta-ur-Rhaman, Ed.; Elsevier: Amsterdam, The Netherlands, 1989; Vol. 3, Part B, p 287.
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