Is there a homolytic substitution chemistry (SH2) of sulfones?
[reaction: see text] A series of 2-alkylsulfonyl-2'-biphenyl radicals, in which the alkyl group is primary, secondary, or tertiary, were generated and the products of their reactions investigated. Dibenzothiophene S,S-dioxide was not identified among the products, which arose mainly from intramolecular hydrogen abstraction from the alkyl group or addition to the solvent, benzene. On this basis, it is concluded that homolytic substitution at sulfonyl sulfur, if possible at all, is too slow to take precedence over a number of competing decomposition pathways. Previous literature results suggesting the possibility of intramolecular homolytic substitution at sulfonyl sulfur may be explained by alternative processes.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Hutton
Thomas K
TK
Ranganathan
Krishnakumar
K
D005609:Free Radicals; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
D005609:Free Radicals; D013450:Sulfones