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MOBILE KETO ALLYL SYSTEMS IN 2-BENZAL-1-INDANONES AND 2-BENZAL-4,4-DIMETHYL-1-TETRALONES
Abstract
Since 1949, when Young and his coworkers first sug- gested that allylic halides can undergo either a normal or an abnormal bimolecular substitution reaction, many papers2-6 concerned with these reactions have been published, and general review articles? 7-8 appeared in literature. summarizing these findings haveMeisenheimer and Link found that x-ethylallyl chloride on treatment with diethylamine or methylamine yielded an ab- normal product, the same one as derived from r-ethylallyl 10 chloride. Also Jones, Lacey and Smith reported the forma- tion of an abnormal product from the action of diethylamine on 2-chloro-hex-3-en-5-yn and 2-chloro-dec-3-en-5-yn. Normal products were obtained with aniline, ammonia and ethylamine. The halides, 1-chloro-pent-2-en-4-yn and 1-chloro-non-2-en-4-yn, yielded normal products even with diethylamine. Jones sug- gested that the formation of abnormal product was attributed to the difference of base strength of the nucleophile.
Subject Area
Organic chemistry
Recommended Citation
WU, E-MING, "MOBILE KETO ALLYL SYSTEMS IN 2-BENZAL-1-INDANONES AND 2-BENZAL-4,4-DIMETHYL-1-TETRALONES" (1966). ETD collection for University of Nebraska-Lincoln. AAI6710686.
https://digitalcommons.unl.edu/dissertations/AAI6710686