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The bromo formylation procedure gave an approximately 10:1 (E)/(Z) mixture of 12, which could not be separated by chromatography. However, subsequent reaction of this mixture afforded the nitrone 16 with no detectable amounts of the corresponding (E) isomer.
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The relatively low yield of 49 (37%) is partly due to the formation of two side-products, namely the primary alcohol of 28 (ca. 20%, isolated as a mixture with 49), obtained by a Grignard reduction process, and a higher molecular compound (ca. 15%, not isolated), which probably comes from the reaction of 28 with the 1,4-bis-Grignard reagent of butane.
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