Photochemically Induced Allylic Hydrogen Abstraction from 1-X-1,2-Dialkylethylenes: Experimental Data and Theoretical Calculations

Article abstract of DOI:10.1021/jo00357a019

Results are presented for the first time concerning the influence of a substituent in directing the allylic hydrogen abstraction.The observed regioselectivity must be attributed only to electronic factors, either mesomeric or inductive, induced by the substituent.A bent transition state, asymetrically bridging the double bond, is postulated to rationalize the experimental data.