152421-79-9Relevant articles and documents
Novel cycloaddition products from the reaction of 2,5-dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene with cycloalkenes, cyclodienes and cycloheptatriene, and of hexafluoroacetone azine with cycloheptatriene
Abdul-Ghani, Mohamad,Tipping, Anthony E.
, p. 5 - 11 (1993)
Thermal reaction (20-70 deg C) of the dichloroazine CF3CCI=N-N=CCICF3 (2) with cyclopentene (in CH2CI2 solwent), cycloheptene, indene, acenaphtylene, 2,3-dihydrufuran, 2,3-dihydropyran, norbornadiene, cyclopentadiene and dicyclopentadiene gives as the major product in each case the rearranged cycloadduct (3) containing a CF3CCI2 group; hydrolisys (CF3CCI2 --> CF3CO) to give the amide (4) takes place on attempted chromatographic purification on silica gel.With cyclopentene the rearrangad cyclopentadiene cycloadduct (3b) is also formed, while other products obtained by chromatographic separation from the 2,3-dihydropylan reaction are the 5,6-dihydropyran-3-yl azine (5), the hydrozone (8) and equimolar quantities of 5,6-dihydropyran-3-yl trifluoromethyl ketone (6) and the chlorohydrazone (7) possible arising via hydrolysis of the 1:2 adduct (16).The reaction of azine 2 with cycloheptatriene at 70 deg C gives a complex mixture, in which the major products are the rearranged cycloadduct (31) and the dehydrochlorinated cycloadduct (10) and (11) containing a CF3CHCI group.The corresponding reaction with hexafluoroacetone azine (1) at 70 deg C affords the criss-cross cycloadduct (22), the bis-ene adduct (23) and its oxidation product, the azo compound (24), and the cycloadduct diaziridine (25).
