Stereochemistry of Eʹ and Eʹʹ decarboxylative-dehydration reactions and the bent bond / antiperiplanar hypothesis orbital model
The known concerted decarboxylative-dehydration reaction of unsaturated hydroxy-carboxylic acids is analyzed through the Bent Bond/Antiperiplanar Hypothesis (BBAH), which considers double bonds as Pauling t bonds. These reactions produce various mixtures of dienes or trienes having either the E or Z configuration. The relative formation of these mixtures of dienes or trienes can be rationalized through the BBAH model by the analysis of resonance structures leading to the antiperiplanar (APP) or the synperiplanar (SPP) electronic delocalization modes.
BBAH #17: P. Deslongchamps, Stereochemistry of Eʹ and Eʹʹ decarboxylative-dehydration reactions and the bent bond / antiperiplanar hypothesis orbital model, Tetrahedron, 2021, 102, 132538-132551.
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