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Pyrroles, thiophenes, and furans
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This chapter discusses pyrroles, thiophenes, and furans. Pyrrole, thiophene, and furan are five-membered ring heteroaromatic compounds containing one heteroatom. They derive their aromaticity from delocalization of a lone pair of electrons from the heteroatom. Consequently, the lone pair is not available for protonation and hence these heterocycles are not basic. Furan is the least aromatic of the trio because oxygen has the greatest electronegativity. The chapter then considers how this variation in aromaticity affects the reactivities of these three related heterocycles. It also looks at the synthesis of pyrroles, thiophenes, and furans, using the Paal–Knorr synthesis. Finally, the chapter reviews the electrophilic substitution and anion chemistry of pyrroles, thiophenes, and furans.
Title: Pyrroles, thiophenes, and furans
Description:
This chapter discusses pyrroles, thiophenes, and furans.
Pyrrole, thiophene, and furan are five-membered ring heteroaromatic compounds containing one heteroatom.
They derive their aromaticity from delocalization of a lone pair of electrons from the heteroatom.
Consequently, the lone pair is not available for protonation and hence these heterocycles are not basic.
Furan is the least aromatic of the trio because oxygen has the greatest electronegativity.
The chapter then considers how this variation in aromaticity affects the reactivities of these three related heterocycles.
It also looks at the synthesis of pyrroles, thiophenes, and furans, using the Paal–Knorr synthesis.
Finally, the chapter reviews the electrophilic substitution and anion chemistry of pyrroles, thiophenes, and furans.
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