The condensation of thianaphthen-2-one and salicylaldehyde gave 6a,lla-dihydro-6H-benzothieno [3,2c] [l]benzopyran-6-one (dihydro-11 -thiacoumestan). Several analogs were prepared. Oxidation of the dihydro compounds with DDQ (2,3-dichloro-5,6-dicyano-l,4-quinone) gave 6H-benzothieno[3,2-c][l]benzopyran-6-ones (11-thiacoumestans), a new heterocyclic ring system, and the sulfur analog of the naturally occurring 6H-benzofuro[3,2-c][l]benzopyran-6-one (coumestan) ring system. The reaction of thianaphthen-2-one with 5-nitrosalicylaldehyde and pyridoxal in alcohol gave the corresponding 2-aryl-2,3-dihydrothianaphthene-3-carboxylates.

From the foregoing, it is apparent that treatment of a complex, substituted hydrocarbon substrate with either elemental fluorine or a fluoroxy reagent (with radical inhibitor) comprises an effective, predictable, and regioselective process for substitution a t saturated carbon.12

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p-Methoxyanisole, p-methylanisole, p-íerí-butylanisole, N,N-dimethyl-p-toluidine, and N,N,N',N'-tetra,methyl-p-phenylenediamine were reduced using lithium-ra-propylamine-iert-butyl alcohol reagent. The anisóles gave results equivalent to the Birch (liquid ammonia) reductions while the anilines gave mainly the tetrahydro derivatives. In the reduction of -di-íerí-butylbenzene and p-dicyclohexylbenzene using lithium-ethylamineethyl alcohol the principal respective products were 1,4-di-íerí-butyl-1,4-cyclohexadiene and l,4-dicyclohexyl-l,4cyclohexadiene. This procedure may provide a general approach for preparing many cyclohexadiene derivatives in good yield and purity, which have not been accessible by any simple methods described hitherto. Upon reduction of 2,3-dimethylnaphthalene with lithium-ethylamine-ethyl alcohol the tetrahydro derivative 2,3-dimethyl-l,4,5,8-tetrahydronaphthalene was formed as the major product. The reduction of -di-íerí-butylbenzene with lithium-ethylamine provided an improved synthesis of 1,4-di-ieri-butylcyclohexene, while reduction of p-diisopropylbenzene afforded 1,4-diisopropylcyclohexene; 1,4-dicyclohexylcyclohexene and 1,4-dimethylcyclohexene were also prepared using lithium-ethylamine.

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