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. ok. 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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Additional resources for Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Part Two, Volume 44
The method has been used to formylate 3-methoxy- and 3-tert-butoxythiophene in the 2 p o s i t i ~ n ~(with ~~,~~' DMA the 2-acetyl derivative was correspondingly obtained). It has been used to formylate 2-butoxythiophene in the 2,5 and 4,5 positions (the latter from 4-bromo3-tert-butoxythiophene), and 3,4-di-tert-butoxythiophene in the 2 and 2,s posit i o n ~ yields , ~ ~ of ~ 30-75% being recorded. ~~~ E. Acetylation and Other Acylations A wide range of methods exist for acylating aromatics in general: 1.
Substitution by Electrophiles 25 B. Protiodeboronation The kinetics of protiodeboronation, which have been studied over a wide range of conditionsi28 are complex. For cleavage by sulfuric acid of various concentraArB(OH), + HX -ArH + B(OH)2X (5) ti on^,"^ the correlation of rate with acidity function varied between substituents in a random manner, so that a linear free-energy correlation of the data must be unsatisfactory. 2), data obtained at lower acidities did not. 47 i h e relative rates were obtained by extrapoiarion of the rate vs.
All of these methods and variations on them, as well as some miscellaneous ones, have been used for acylating thiophene and its derivatives. One of the primary problems in these reactions is the degrading effect upon thiophene of the acid catalysts, and also the fact that these and the acidic by-products of reaction may lower the reactivity of thiophene either through hydrogen bonding or, more severely, by forming protonated complexes. Consequently, methods using milder conditions, such as mixed anhydrides without catalysts, have been investigated in recent years, but even with these, strong acids are of necessity produced as reaction by-products.