By Salo Gronowitz
Electrophilic Sustitution of Thiophene and Its Derivatives (R. Taylor).
Alkylthiophenes and Their Reactions (P. Cagniant, et al.).
Halothiophenes and Their Reactions (M. G. Reinecke & P. Padaja).
Nitrothiophenes and Their Reactions (R. okay. Norris).
Aminothiophenes and Their Derivatives (R. ok. Norris).
Chapter I Electrophilic Substitution of Thiophene and its Derivatives (pages 1–117): Roger Taylor
Chapter II Alkylthiophenes and their Reactions (pages 119–158): P. Cagniant, D. Cagniant, D. Paquer and G. Kirsch
Chapter III Halothiophenes (pages 159–522): Manfred G. Reinecke and Peter Pedaja
Chapter IV Nitrothiophenes and their Reactions (pages 523–629): Robert okay. Norris
Chapter V Aminothiophenes and their Derivatives (pages 631–799): Robert okay. Norris
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Extra info for Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Part Two, Volume 44
6 is thus very reliable (a higher value applies if the Yukawa-Tsuno equation is used). These ~ ~ give u+ values in very good agreement with those determined from a number of other reactions (Table 2); both positions are less reactive in desilylation than the corresponding positions in f ~ r a n . 1 X the substituent effects with those in benzene is more relevant than for most other studies of this type because of the wide range of substituents used in both systems. They show that the p factor for thiophene is ca.
3-Methyl-2-phenylthiophene gave a 69% yield of the 5-formyl deri~ative,’~’which seems rather low in view of the other results. 3-Phenylthiophene 39 gave 94% 2- and 6% 5-substitution,230the greater amount of the minor component compared to 2-phenylthiophene reflecting the difference in the 2:3 positional reactivities in thiophene. 3-Methyl and 3-bromothiophenes gave 33 and 70% overall yields, respectively, of a 7 : l mixture of the corresponding 2and 5-formyl derivative^,'^^ thereby showing the greater ortho- vs.
Chloroalkylation (strictly it ,should be classed as alkylation) has been carried out using 3-chloro-2-methylpropene,which with catalysis by boron trifluoride etherate gave 2-(2-chloro-1,1-dimethylethyl)thophene30, together with some of the 2,5disubstituted product; formation of the latter was suppressed using BF3-Hz0 as catalyst. 21s Me 31 D. Formylation Introduction of the formyl group into an aromatic ring can be effected with the following electrophilic reagents: (i) (ii) (iii) (iv) CO -t HC1+ Lewis acid (Gatterman-Koch reaction) HCN -t HCl + Lewis acid (Gatterman reaction) C1,CHOMe -t HCl -t Lewis acid, followed by hydrolysis HCONMe, (or HCONMePh) + POC13 (or COCl,) (Vilsmeier-Haack reaction) The former two reactions using aluminium chloride as the catalyst were reto give very low yields with thiophene, and the reason for this is probably decomposition of the thiophene by the catalyst.