A new series of vitamin e (α-Tocopherol) bearing 1,2,3-thiadiazole and selenadiazole derivatives (4, 5, 9a-d and 10a-d) were isolated by using thionyl chloride and selenium dioxide respectively with α-tocopherol/semicarbazone derivatives (3 and 8a-d) as precursor compounds. The equivalent reaction with tellurium dioxide did not yield the related α-tocopherol fused 1,2,3-telluradiazole derivatives. The newly synthesized compounds 4, 5, 9a-d and 10a-d were evaluated against four bacteria Bacillus subtilis and Staphylococcus aureus (Gram-positive bacteria) and Pseudomonas aeruginosa and Salmonella typhimurium (Gram-negative bacteria). The results of bioassays indicated that the compounds 4-(α-tocopheryl) methyl)-1,2,3-thiadiazole (4) and 5-(4-substitutedphenyl)-4 -(α-tocopheryl) methyl)-1,2,3-thiadiazole (9a-c) displayed broad spectrum against both Gram-positive and Gram-negative bacteria. Derivatives 4-(α-tocopheryl) methyl)-1,2,3-selenadiazole (5) and 5-(4-substitutedphenyl)-4-(α-tocopheryl) methyl)-1,2,3-selenadiazole (10a-d) have moderate activity against Gram-positive bacteria. Spectroscopic methods IR, ¹H-NMR, ¹³C-NMR, Mass spectra and elemental analysis have been used to elucidate and validate all newly synthesized compounds.