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note
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EE-FHD was prepared by fluorination of trans,trans-1-bromo-2,40-hexadiene-1-ol (97%, Aldrich) with phosphorous bromide. The product mixture (ca. 70% EE-FHD) was purified by preparative gas-phase chromatography (6′ x 18″ column packed with chromosorb W coated with 10% OV-17) to yield a pure sample of EE-FHD (99.5%).
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24
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note
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A 2 mM EE-FHD solution was photolyzed at 0° in capillary quartz tubes with low-pressure Hg lamps (G25t8). The photoreaction was monitored using analytical GC (30 ni x 0.25 μm x 0.25 mm AT-50 capillary column). Regioselectivities were determined by measuring the yields of ZE and EZ-FHD at times corresponding to less than 6% conversion of EE-FHD.
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