SYNTHESIS AND REACTIONS OF UNSYMMETRICAL DISULFIDES AND DISULFONES. RING-CLOSURE REACTIONS OF BETA-ARYLETHYL DISULFIDES.
Quarterly status rept. no. 1, 1 Jan-31 Mar 61,
INDIANA UNIV BLOOMINGTON
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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-bthiophene. Using excess iodine, the product is mainly naphtho1,2-b thiophene. These products were identified by conversion to picrates and oxidation to naphtho1,2-bthiophene-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