Cyclization mechanism and syntheses of N-(B-Chlorethyl)-benzenosulfonamides

Thesis (M.A.)--Boston UniversityPLEASE NOTE: Boston University Libraries did not receive an Authorization To Manage form for this thesis or dissertation. It is therefore not openly accessible, though it may be available by request. If you are the author or principal advisor of this work and would like to request open access for it, please contact us at open-help@bu.edu. Thank you.Reactions in which halogen on a beta carbon atom is internally displaced by nitrogen are well known and have been studied in the past. Most of the work has been done where nitrogen was in the form of an amine. No work had been previously carried out where nitrogen was in the form of a sulfonamide. The preparation of various B-halo substituted benzenesulfonamides and the investigation of the kinetics of ring closure of a select few of these compounds forms the main body of this thesis. The synthesis of the B-halobenzenesulfonamides was carried out in several ways. In some cases, allylamine was treated with benzenesulfonyl chloride and subsequently brominated. By a series of cyclizations with alkali and ring ruptures with the appropriate halogen acid, the 1,3-dihalo-2-benzenesulfonamidopropanes were prepared. For some compounds the B-haloamine was readily purchased and was combined directly with benzenesulfonyl chloride. In one case, propylenimine was reacted with benzenesulfonyl chloride and the imine ring was ruptured with the appropriate halogen acid. Some of the compounds had been prepared previously and were reported in the literature. Where new compounds were prepared, their structures were proven by analysis for carbon, hydrogen, nitrogen and halogen and also by analysis of the infrared spectra of the compounds.2031-01-0