Molecular baggage

In the foregoing examples, the latent nucleophiles were intrinsic to the protecting group and as such were part of the molecular baggage that had to be carried through a synthetic sequence. Scheme 8.2855 illustrates the cleavage of an N-chloroacetyl group in which the nucleophile is appended at the time of deprotection by 5-alkylation of piperidinethiocarboxamide.56 Thiourea will accomplish the same task.57,58... 

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