Pyrolysis of N,N-Dihalo Derivatives of Amides and Sulfonamides

Article abstract of DOI:10.1021/jo00333a010

Pyrolysis of N,N-dichlorobenzenesulfonamide produced benzene (41percent) and chlorobenzene (40percent); the dibromo compound gave benzene (19percent) and bromobenzene (20percent).Toluene (46percent), chlorotoluene (27percent), and dichlorotoluene (10percent) were generated from the N,N-dichloro-p-tolyl derivative.From each aryl substrate, 1,1,2,2-tetrachloroethane was also produced from reactions involving CH2Cl2 solvent. 3-Chloro-N,N-dichloroadamantane-1-sulfonamide decomposed to 1,3-dichloroadamantane (52percent) and 1,3,5-trichloroadamantane (15percent).N,N-Dihalobenzamides produced phenyl isocyanate; N,N-dichloro and N-bromo derivatives gave isocyanate in 16-23percent and 21-28percent yields, respectively.N,N-Dichloroadamantane-1-carboxamide produced 1-adamantyl isocyanate (20-50percent) and 1-chloroadamantane (12-46percent).The mechanistic features of the various reactions are discussed.