Benzene derivatives 2a-c with 6, 4, and 3 side chains bearing terminal
1,2,3-thiadiazole rings, respectively, have been prepared. Alkaline c
leavage of 2a-c led to the corresponding alkynethiolates 6a-c, which w
ere trapped by electrophiles such as benzyl bromide or iodomethane. Th
e method provides and alternative to the thermal or photochemical clea
vage of 1,2,3-thiadiazoles to thioketenes, which react further with nu
cleophiles.