Reactions of Side-Chain Substituents in the Selenophene Series

Reactions of Side-Chain Substituents in the Selenophene Series [Pg.30]

This section of the review is concerned with reactions in the side-chain of selenophene derivatives, in which the heterocyclic nucleus exerts an influence, but is not directly attacked. [Pg.30]

The chlorine atom of chloromethyl derivatives of selenophene is very reactive and easily displaced in substitution reactions. Thus, 2-chloromethylselenophene and its homologs readily exchange the chlorine for dialkylamino, alkoxy, and acetoxy groups, and the chloromethyl can be converted into an aldehyde group, providing a synthesis for 2,5-dimethylselenophene-3-aldehyde (7) which cannot be obtained by direct formylation.102 [Pg.30]

Selenophene chloromethyl derivatives readily form di(/3-hydroxy-ethyl)aminomethylselenophenes (8) which, with thionyl chloride, give the corresponding di(/3-chloroethyl)aminomethylselenophenes (9).103 Chloromethylselenophenes condense with trisubstituted ethylene-diamines to yield tetrasubstituted diamines containing the selenophene nucleus.104 The reaction of 2-chloromethylselenophene with sodium derivatives of malonic and acetoacetic ester yields the acid (10) and ketone (11), respectively, whereas with alkyl magnesium halides 2-(alkylmethyl)selenophenes are formed.105 [Pg.30]

halomethyl selenophenes are highly reactive and in their properties closely resemble the corresponding thiophenes. [Pg.31]

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