General approach to cycloalkanone synthesis. Intramolecular alkylation of 2-chloro-1-olefins

PT Lansbury, EJ Nienhouse, DJ Scharf…

Index: Lansbury,P.T. et al. Journal of the American Chemical Society, 1970 , vol. 92, # 19 p. 5649 - 5657

Full Text: HTML

Citation Number: 25

Abstract

Abstract: Various cyclic ketones can be synthesized by incorporating allylic-vinylic dichlorides, eg, 2, 3-dichloropropene, into reaction sequences originating with nucleophilic displacement at the allyl carbon. The relative inertness of vinyl chlorides allows various intervening chemical transformations of the adducts to be carried out, and minimizes the problem of haloalkene isomerization. Cycloalkanone formation is completed by ...