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18.6.5.1.2.5.1 Variation 1: Thermal Isomerization of O-Aryl Thiocarbamates

DOI: 10.1055/sos-SD-018-00578

Rossi, L.Science of Synthesis, (200518614.

An elegant path to S-aryl thiocarbamates 314 is the thermal rearrangement (NewmanKwast rearrangement) of O-aryl thiocarbamates (Scheme 221). This reaction is formulated as an intramolecular four-membered ring process. An analogous process occurs with O-allyl thiocarbamates; in this case the thermal conversion of O-allyl thiocarbamates into S-allyl thiocarbamates is described as a [3,3]-sigmatropic rearrangement.[‌526‌,‌527‌]

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