84766-36-9Relevant academic research and scientific papers
ELECTRONIC EFFECTS ON THE REGIOSELECTIVITY IN THE REACTIONS OF THIOALLYLIC ANIONS WITH CARBONYL COMPOUNDS
Baba, Hideo,Hayashi, Toshio,Oishi, Takeshi
, p. 3852 - 3855 (2007/10/02)
In the reactions of lithium salts of allylic N,N-dimethyldithiocarbamates with p-substituted aromatic aldehydes and ketones, the α-selectivity increases as the substituent of the phenyl ring becomes more electron-attractive.The regioselectivity also depends upon the substitution pattern of the allylic moiety.The Hard and Soft Acid and Base (HSAB) approach was used to rationalize the results.KEYWORDS-thioallylic anion; allylic dithiocarbamate; regioselectivity; HSAB approach; electronic effect
