Some New Chlorinated Substances Starting from Propiophenone

摘要

Some chlorinated derivatives starting from propiophenone were prepared and are described for first time: alpha,alpha-dichloropropiophenone (II), alpha,alpha,beta,beta-tetrachloropropylbenzene (III), alpha,beta-dichloropropenylbenzene (IV), 1H-eneanochloroindan (V), and gamma-H,gamma-H,2H-eneanochloropropylbenzene (VII). The characterization of V and VII were accomplished mainly on the basis of their ultra-violet and infra-red spectra. The ultra-violet spectrum of perchloroindan is also reported for first time. It is shown that chlorination of III under the nuclear chlorinating conditions described by Ballester et al.(JACS v82 p4254 1960) can result in side-chain ring closure with the benzene ring. Photochlorination of VII gives also such type of annelation. Also, it is shown that under those chlorinating conditions chlorine addition to ethylene bond, as well as side-chain substitution of hydrogen by chlorine, takes place. (Author)