PHIL 2130 Chapter Notes - Chapter 3.0: Sulfoxide, Sulfone, Thioether
6 May 2020
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Thiol sulfhydryl group (r-s-h) oxidized to sulfonic acid. Thioether sulfur bound to two aliphatic groups (r-s-r") Oxidized to sulfone: oxidation of h-atom to oh formation of sulfenic acid, s from second sulfhydryl group lone pair used to oxidize sulfenic acid. Result = disulfide formation and loss of ve hydroxyl: hydroxyl nucleophilic attack on s (x4) formation of sulfonic acid, sulfur oxidized to s=o to form sulfoxide. Reversible reaction can be reduced back to thioester: sulfoxide oxidized to sulfone. N-dealkylation/n-deamination breakdown of 3 amine to aldehyde + 2 . Products of n-dealkylation/n-deamination amine: oxidation of h-atom on alkyl group to oh, loss of proton from oh to form carbonyl. Electrons in c-n bond move to more electronegative n-atom. Result = breaking bond between c-n -ve amine + carbonyl: ve n-atom picks up h-atom to form 2 amine. Result = aldehyde + amine: aldehyde oxidized to carboxylic acid. Two adjacent carbons with atoms both can be oxidize.
