76463-83-7Relevant articles and documents
CYCLOADDITION REACTIONS OF 4,6-DIPHENYLTHIENO-1,2,5-OXADIAZOLE AND -1,2,5-THIADIAZOLE WITH 6,6-DIPHENYLFULVENE AND TROPONE
Tsuge, Otohiko,Takata, Toshiaki,Noguchi, Michihiko
, p. 1031 - 1034 (1980)
4,6-Diphenylthieno-1,2,5-oxadiazole (1) reacts as a thiocarbonyl ylide with 6,6-diphenylfulvene to give the exo- adduct via a stereoselective and regiospecific cycloaddition.The exo-adduct undergoes thermal cleavage of the oxadiazole ring to nitrile and nitrile oxide moieties which can be trapped as 1,3-cycloadducts to the fulvene and dimethyl acetylenedicarboxylate.The reaction of 4,6-diphenylthieno-1,2,5-thiadiazole (2) with the fulvene affords a mixture of analogous exo- and endo-adducts which are subject to a retro-cycloaddition reaction.On the other hand, 1 reacts with tropone to give the corresponding adduct which is susceptible to a retro-cycloaddition reaction.However, 2 did not react with tropone.