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22.7.3.1.2.4.2 Variation 2: Addition of Allylsilanes to Trithiocarbonates

DOI: 10.1055/sos-SD-022-00871

Lebel, H.; Grenon, M.Science of Synthesis, (200522765.

Allylsilanes also bind to the sulfur atom of diphenyl trithiocarbonate (43) to provide trithioortho esters 55 in moderate to good yields (Scheme 16).[‌69‌] These fluoride ion-promoted reactions proceed with complete regiochemical control, and no products arising from an allyl shift or a double bond isomerization are observed. Trimethylbenzylsilane behaves in a similar way, yielding the expected trithioortho ester in good yields.

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