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22.1.3 Product Subclass 3: Thiocarboxylic O-Acid Esters

DOI: 10.1055/sos-SD-022-00101

Glass, R. S.Science of Synthesis, (20052285.

General Introduction

Thiocarboxylic O-acid esters and thionolactones are reactive species that are very useful in synthesis.[‌1‌,‌2‌] In analogy with the synthesis of carboxylic acid esters by acylation of alcohols, they can be made by thioacylation of alcohols.[‌1‌‌5‌] Thiocarboxylic O-acid esters can also be made from carboxylic acid esters by replacement of the acyl oxygen with sulfur.[‌1‌,‌2‌,‌6‌‌13‌] Imino ethers formed either by O-alkylation of carboxamides or acid-catalyzed addition of alcohols to nitriles react with hydrogen sulfide to produce thiocarboxylic O-acid esters.[‌1‌,‌2‌,‌14‌‌18‌] Alkoxythiocarbonylation of enolates is a viable route to β-oxo thiocarboxylic O-acid esters.[‌2‌,‌19‌‌21‌] Elimination reactions from monothioacetals to generate ­thi­onolactones involving photochemical Norrish type II or sulfoxide eliminations are known[‌22‌,‌23‌] and are advantageous in some cases.

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