https://www.selleckchem.com/pr....oducts/n6-methyladen
Hyperconjugation/conjugation through-bond stereoelectronic effects were studied with density functional theory in the context of 3-azabicyclo[3.3.1]nonanes to unravel puzzling differences in reactivity between a vinylogous chloride (4) and a vinylogous ester (5). These compounds─whose structures differ only by one substituent─were found to display strikingly different reactivities in hydrochloric acid by Risch and co-workers ( J. Am. Chem. Soc., 1991, 113, 9411-9412). Computational analyses of substituent effects, noncovalent
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