Preparation of Symmetrical Diaryl Disulfides Containing Side Chains Terminated by Halogen or by Tertiary Amino Functions

Abstract

Various methods of preparation for a number of new symmetrically substituted diaryl disulfides containing (a) such side chain halogen or pseudo halogen-containing functions as ω-haloalkyl-, ω-haloacyl-, and ω-tosyloxyalkyl-, e.g., bis(4-β-bromoethyl- 1-naphthyl) disulfide, bis(4-γ-chloropropoxy-1-naphthyl) disulfide, bis(2-chloroacetamidophenyl) disulfide, bis(4-β- tosyloxyethoxy-1-naphthyl) disulfide, and bis(2-chloroacetophenyl) disulfide, and (b) such side chain tertiary amino functions as the isonicotinoyl-, ω-4-pyridylalkyl-, or ω-dimethylaminoalkyl, e.g., bis(2-isonicotinamidophenyl) disulfide, bis[2-β-(2′,4′- pvridylethylthio)propionamidophenyl] disulfide, and bis(4-β-dimethyIaminoethoxycarbonyl-2,6-xylyl) disulfide, are described. Chain transfer constant values of a number of these diaryl disulfides (as determined for bulk styrene polymerization at 50°) as well as other physical properties and data relating to the preparation of these disulfides and their intermediates are recorded. © 1958, American Chemical Society. All rights reserved.