Rearrangements Connected with the Migration of Acyl and Certain Other Groups

This review surveys instances of the migration of groups sensitive to nucleophilic attack (structures exhibiting the $\mathrm{C}=\mathrm{O}$; $\mathrm{C}=\mathrm{S}$ or $\mathrm{C}=\mathrm{N}$ bonds) between two nucleophilic groups ($\mathrm{NH}_2$; $\mathrm{OH}$, and $\mathrm{SH}$). Intramolecular rearrangements connected with the migration of acyl groups in acylated amino-phenols, amino-alcohols, polyhydric alcohols and phenols, diamines, thioglycols, amino-thiophenols, and amino-thiols are considered. The rearrangements take place by a common mechanism through the stage of formation of unstable cyclic compounds. Apart from the migration of acyl residues, instances of the rearrangements associated with migration of other groups which proceed by an analogous mechanism are surveyed in the article. Such rearrangements
\begin{gather} \biggl(\begin{smallmatrix} -\mathrm{C}\equiv\mathrm{N}; &\mathrm{H}_2\mathrm{N}&&\mathrm{H}_2\mathrm{C}-\mathrm{N}&\\ & & \geqslant\mathrm{C}-;&|&\eqslantgtr\mathrm{C}-,\,\text{with}\,\mathrm{X}=\mathrm{O};\mathrm{S};\ \mathrm{NH};\\ &\mathrm{HN}& &\mathrm{H}_2\mathrm{C}-\mathrm{X}& \end{smallmatrix} \notag\\ \begin{smallmatrix} \mathrm{S} &\mathrm{S} \\ \parallel & \parallel\\ \mathrm{R}_2\mathrm{N}-\mathrm{C}-;&\mathrm{RO}-\mathrm{C}-\,\text{etc.} \end{smallmatrix}\biggr), \notag \end{gather}
are not only of theoretical interest but are also of great importance for preparative practice.
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