In recent years, thiocarbonyl ylides found new application as useful buildi
ng blocks in syntheses of sulfur containing heterocycles. They were also sh
own to play an important role as key intermediates in two-step [3+2] cycloa
ddition reactions. Strategies explored for the generation of thiocarbonyl y
lides and their typical reactions including [3+2] cycloadditions, 1,3- and
1,5-electrocyclizations, additions of OH, SH, and NH groups, and rearrangem
ents are presented. Reactivities of isolable, push-pull stabilized thiocarb
onyl ylides are compared with those proposed as transient species.