Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 19, Pages 7672-7678Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo050990c
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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.
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