3.

3 Heterocyclic Chemistry

Reactivity of Pyrrole furan and

thiophene and pyridine
Reactions of furan

Dr. Krishnakant T. Waghmode

Associate professor
Department of Chemistry
 Reactivity of furan thiophene and pyrrole

6 pi electrons are delocalized over 5 atoms hence it is pi excessive compo

and undergo electrophilic substitution reactions like nitration, halogenatio
sulphonation etc.
Resonating structures 3 and 4 are most stable because of
less charge separation
Hence SE reactions take place at 2 and 5 positions

 It can be explained based on the relative stabilities of the intermediate carbocations formed during the
SE reactions.
 Attack at 2-position
b. Reactivity of Pyridine
SE and SN reactions in Pyridine
 Reactions of Heterocycles

 A. REACTIONS OF FURAN:
 1. Halogenation:
 ii.Nitration:

-5 DEGREE
 iii. SULPHONATION:
 iv-FRIEDEL CRAFTS ALKYLATION

 Alkylation cannot be carried out as it results in polyalkylated product. Further

AlCl3 cannot be used as it forms complex with furan.
 Therefore acylation can be carried out by using acetic anhydride in presence
of BF3- ether at low temperature.

BF3-Ether O
(CH3CO) 2O O
+ o °C + H3C
O
O OH
CH3
 V. Vilsmeyer-Haack reaction

H3C NaOH
PoCl3 + O
- N
+ (CH3)2N CHO
 CH
CH3 H2O O
O
O H
H3C
+ N H
H3C
 VI. DIELS-ALDER REACTION OF FURAN
VI. RING OPENING REACTION OF FURAN
References

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