Sulfides naphthyl, formation

Attempted preparation of 3-phenylbenzo[6]thiophenes by an extension of the above method invariably proceeds with rearrangement to give the 2-phenyl isomer186,299,303,304,307 308 or a mixture of the 2- and 3-phenyl isomers.186,308 In this case, use of PPA appears to favor formation of the 3-isomer,186,299, 309 whereas use of hydrofluoric acid usually affords the 2-isomer.299 It is interesting to note that 3-phenylbenzo[6]thiophene is converted into its 2-isomer by hydrofluoric acid,290 but is only isomerized to a small extent by hot PPA.186,308 During the cyclization of phenyl phenacyl sulfide to give 2- and/or 3-phenylbenzo[6]thiophene, small amounts of diphenyl disulfide and 5-phenylmercapto-3-phenylbenzo[6]thiophene are also formed.186,209 3,3 -Dibenzo[6]thienyl,305 2,3 -dibenzo[6]thienyl,305 and mixtures of 2- and 3-(2-thienyl)benzo[6]thiophene, 2- and 3-(2-naphthyl)benzo[6]thiophene, and 3-(1-naphthyl)- and 2-(2-naph-thyl)benzo[6]thiophene309 have been prepared by the appropriate modification of the Werner procedure. 

Lewis acid, In(0CF3S02)3, catalysed allylic C—H oxidation of aryl cycloalkenes by l-(propyl thio)pyrrolidine-2,5-dione in the presence of CH2CI2 and various nucleophiles (ROH, RCO2H, RSO2NH2) resulted in the formation of allylic ethers, esters, and sulfonamides in 52-83% yields electron-rich substrates were the most reactive. Other aryl cycloalkenes such as 1-naphthyl, l-(3-thiophenyl)-cyclohexene, 1-phenylcycloheptene, and 1-phenylcyclopentene were suitable substrates. Mechanistic studies showed that the sulfenamide played an important role in converting the allyl sulfide intermediate into the products. ... 

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