a De part ment of Chem is try, Chung-Yuan Chris tian Uni ver sity, Taoyuan, Tai wan, R.O.C. b De part ment of Chem is try, Soochow University, Tai pei, Tai wan, R.O.C.Tan dem cas cade re ac tions of allyl azides and olefinic dipolarophiles to give cis-fused 2,3,7-t riazabi cyclo [3.3.0]octenes (5, 6 or 7) are re ported. Therein, an intermolecular dipolar cycloaddition of azide and alkene gave a triazoline which was fol lowed by isomerization of the triazoline to a diazo es ter (4) and then an intramolecular dipolar cycloaddition from the diazo func tional group and the dou ble bond in 4 to give 5. Compound 5 may fur ther more un dergo a Mi chael ad di tion to give 7-substituted-2,3,7-triazabicyclo [3.3.0] oct-2ene ( 6) or a tautomerization to give 2,3,7-triazabicyclo[3.3.0]oct-3-ene (7). The re ac tion may be ma nip u lated to stop at a par tic u lar stage by adopt ing a suit able sol vent or an ap pro pri ate tem per a t ure.
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