Abstract
Trichloromethanesulphonyl chloride reacts with hept-1-ene, with propene, and with 1,1,1,3-tetrachloro-cyclohexene to give octane, 1,1,1,3-tetrachlorobutane, and 1-chloro-2-trichloromethylcyclohexane respectively, together with sulphur dioxide and small amounts of chloroform and carbon tetrachloride. Dichloromethanesulphonyl chloride, for which a new synthesis is described, and chloromethanesulphonyl chloride react with hept-1-ene in the presence of benzoyl peroxide to give 1,1,3-trichlorooctane and 1,3-dichlorooctane respectively. A general mechanism is proposed for these reactions, which are free radical in type. Reductive cyclisation of 1,3-dichlorooctane with zinc gives n-pentylcyclopropane, providing a new route from alkenes to alkylcyclopropanes. In agreement with structral assignments, reduction of each of 1,1,1,3-tetrachlorooctane, 1,1,3-trichlorooctane, and 1,3-dichlorooctane with LiAlH 4 gives n-octane, with lesser amounts of n-pentylcyclopropane.
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