Chemoselective Rearrangement Reactions of Sulfur Ylide Derived from Diazoquinones and Allyl/Propargyl Sulfides.

Here, we describe three types of rearrangement reactions of sulfur ylide derived from diazoquinones and allyl/propargyl sulfides. With Rh(esp) as the catalyst, diazoquinones react with allyl/propargyl sulfides to form a sulfur ylide, which undergoes a chemoselective tautomerization/[2,3]-sigmatropic rearrangement reaction, a Doyle-Kirmse rearrangement/Cope rearrangement cascade reaction, or a Doyle-Kirmse rearrangement/elimination reaction, depending on the substituent of the sulfides. The protocol provides alkenyl and allenyl sulfides and multisubstituted phenols with moderate and high yields.