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Title
| - Effective and Highly StereoselectiveCoupling with Vinyldiazomethanes ToForm Symmetrical Trienes
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Abstract
| - Diazo coupling reactions are capable of formingE,E,E-trienes from cinnamaldehydes in good yield. Anefficient methodology is reported for the production of styryldiazomethanes that are subsequently used with catalysis forcoupling and for cyclopropanation. A vast difference inproduct selectivity is seen with styryldiazomethane generated from the corresponding hydrazone via manganesedioxide oxidation and that formed in situ by treatment ofthe tosylhydrazone sodium salt of cinnamaldehyde withtransition metal catalysts. This observation impacts understanding of the reaction mechanism for diazo decomposition.
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