Ω-Haloalkyl AND Ω -AMINOALKYL SULPHIDES CLEAVAGE OF THE ALKYL–SULPHUR BOND

Abstract

In the homologous series of p-chlorophenyl w-chloroalkyl sulphides (I), the first and second members reacted abnormally with amines to yield 1,w-bis(p-chlorophenylmercapto)allcanes (11). The fourth member of the series reacted 11ormally to produce 4-aminobutyl p-chlorophenyl sulphidc (111). The formation of I1 is explained on the basis of an alkyl-sulphur bond cleavage. The members of the p-chlorobenzyl series (VI) in general reacted with a~nines to form the cspected aminoalkyl sulphides (VII). However, the p-chlorobenzpl chloroalkpl sulphides (VI) were thermally labile and decomposed to p-chlorobenzpl chloride and a sulphur component. A cyclic sulphur component originated from VI whose chloroalkpl carbon chain was 4, 5, or 6. The thermal degradation of VI is explained t h r o~~g h a s~~lphonium salt cleavage. INTRODUCTIONI t has been recently shown that p-chlorophenyl chloro~nethyl sulphide (I, n = 1) can undergo an unusual bin~olecular reaction to form 2,8-dichloro-GH,12H-dibenzo(b,f)-1,sdithiocil~ (1). Now another anomalous reaction of I has been discovered and is the subject ~il.ianuscript receioed Septcnzber 18, 1058.