Ring opening in di[1,2,3]triazolo-[1,3,6]thiadiazepine and -[3,1,5]benzothiadiazepine in reactions with butyllithium

Di[1,2,3]triazolo[1,5-a:5’,1’-d][3,1,5]benzothiadiazepine treated with butyllithium undergoes ring opening via the thiophilic addition of butyllithium at the C–S bond, whereas 9,10-dihydrodi[1,2,3]triazolo[1,5-b:5’,1’-f][1,3,6]thiadiazepine mainly undergoes lithiation of the methylene group followed by C–N bond cleavage to give 1-vinyltriazolyl sulfide.