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20.8.4.1.4 Method 4: Synthesis by Rearrangement

DOI: 10.1055/sos-SD-020-01480

Collier, S. J.Science of Synthesis, (2007201634.

Thiocarboxylic acid S-esters can be prepared by a number of rearrangement reactions, ranging in complexity from simple to moderately complex. Simple reactions include the thermal isomerization of thiocarboxylic acid O-esters (e.g., 78) to give the thermodynamically more stable thiocarboxylic acid S-esters (e.g., 79); (Scheme 31).[‌326‌‌330‌] Other rearrangement reactions include the base-mediated rearrangement of pyran-2-thiones to thiopyran-2-ones by a hydrolysisconjugate additiondehydration sequence,[‌331‌‌333‌] and the photolytic rearrangement of 4-hydroxyphenacyl sulfides to S-alkyl (4-hydroxyphenyl)ethanethioates, although yields in this reaction are often low.[‌131‌]

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