SYNTHESIS AND REACTIONS OF UNSYMMETRICAL DISULFIDES AND DISULFONES. RING-CLOSURE REACTIONS OF BETA-ARYLETHYL DISULFIDES.
Abstract
Bis-o-biphenylyl disulfide was found to cyclize to dibenzothiophene in excellent yield when treated with iodine in refluxing ethylene glycol. Under similar conditions, bis-beta-2-naphthylethyl disulfide gave a poor yield of 2,3-dihydronaphtho-(1,2-b)thiophene. Using excess iodine, the product is mainly naphtho(1,2-b) thiophene. These products were identified by conversion to picrates and oxidation to naphtho(1,2-b)thiophene-1,1dioxide. Bis-1-phenylcyclohexyl disulfide, prepared from X-acetyl-2-phenylcyclo-hexanethiol, could not be cyclized under the influence of iodine in ethylene glycol. A large percentage of the disulfide was recovered, along with some biphenyl. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Apr 25, 1961
- Accession Number
- AD0614690
Entities
People
- B. G. Heaton
- E. Campaigne
Organizations
- Indiana University Bloomington