By H. D. Hartough
Content material:
Chapter I elements Influencing Chemical Reactivity and Substitution of Thiophene structures (pages 1–16):
Chapter II Thianaphthene and different Thiophene Compounds Containing one Carbocyclic Fused Ring (pages 17–174):
Chapter III Thioindigo and similar Dyes (pages 175–224):
Chapter IV Dibenzothiophene and its Derivatives (pages 225–282):
Chapter V Naphthothiophenes and different Thiophene Compounds Containing Carbocyclic Fused earrings (pages 283–313):
Chapter VI Thiophene platforms Containing 3 or extra Carbocyclic Fused jewelry (pages 315–355):
Chapter VII Condensed Thiophene Compounds Containing O, S, and HG Ring structures (pages 357–402):
Chapter VIII Condensed Thiophene Compounds Containing Nitrogen Ring structures (pages 403–446):
Chapter IX Condensed Selenophene and Tellurophene structures (pages 447–461):
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Additional resources for Chemistry of Heterocyclic Compounds: Compounds with Condensed Thiophene Rings, Volume 7
Sample text
It is also prepared by the method described in equation 2 from 2-wpropylthiophenol (280). Pure 3-methylthianaphthene cannot be isolrtted when this reaction is applied to 2-isopropylthiophenol. Werner (525) obtained %methylthianaphthene by dehydration of phenyl acetony1 sulfide (eq. 8). 3Methylthianaphthene, as well aa the 3-ethyl homolog, haa been prepared 23 Physical Properties of Thianaphthene TABLE 11-1. Physicnl Properties of Thhphthene Rei. , "C. ).. , OC... . . . . . * . 279,102,386,745 327 228 547 194 ...........................
It can be converted to 3-thianaphthenecarboxylic acid through a t y p i d Grignard synthesis (133,329,331,518). A series of complex r e actions takea place when 3-bromothianaphthene is reacted with potsssium hydroxide in methanol (329) (eq. 44). Thianaphthene (I) was obtained in (11) (1) (111) about 10% yield while I1 W&B the major product. This was identified by convemion to diphenyldisulfide-2,2’-diaceticacid by treatment with methanolic sodium hydroxide. The formation of 11 probably took place upou acidulation of the potassium salt of o-mercaptophmylacetic acid in the isolation procedure.
OI md. 0-8* NO* I 1. 2. Bnch, C g c o O a EN& quite similar to that described for the polymerization of thiophene (603). 2,2'-Bithianaphthene also results from the coupling action of bromine on 2-thianaphthenyllithium (736). 3-(1-Cyclohexeny1)thianaphthene has been prepared by condensation of cyclohexanone and 3-thianaphthenylmagnesium bromide (537) (eq. 21). 3-(3',4'-Dihydro-l'-naphthyl)thianaphthene was synthesized in the same manner from a-tetralone and was dehydrogenated to give 3-( I'-naphthy1)thianaphthene by heating with sulfur at 220-240" (537).