Chloromethyl selenophenes reactions

Catalysts (ZnCl2, SnCl2, H3P04, or P0C13) sharply decrease the reaction yield. Methyl selenophenes are chloromethylated under milder conditions than the unsubstituted compound, and 3-methyl-selenophene is chloromethylated easier than the 2-methyl compound.60... 

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... 

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... 

Selenophene-2,5-dicarboxylic acid, cis-tetrahydro-synthesis, 4, 962 Selenophenes, 4, 935-971 acetylation, 4, 948 alkylation, 4, 948 annelation, 4, 969 applications, 4, 971 aromaticity, 4, 30 bromination, 4, 947 chloromercuration, 4, 83 chloromethylation, 4, 54 cycloaddition reactions, 4, 67, 950 deprotonation, 4, 59 /3-diketones applications, 4, 971 a-directing effect, 4, 44 2,5-disubstituted synthesis, 4, 964, 965 electrophilic substitution, 4, 43, 946 formylation, 4, 946, 948 with fused six-membered heterocyclic rings, 4, 973-1036... 

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