Diels-Alder Cycloadditions of Sulfonyl Cyanides with Cyclopentadiene. Synthesis of 2-Azabicyclo[2.2. l]hepta-2,5-dienes

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A solution of o,69 (2 mmoles) of and o,53,g (2 mmoles) of in 20 ml of ethanol and I drop ofacetic acid13 was refluxedfor 36 h. The precipitate was collected and washed with boiling ethanol. The residue was crystallized from chloroform-petr. ether (b.p. 80-1 IOOC) giving 0.75 g (61 "/.) of 9; m.p. 215-217OC; NMR (CDCI,): 6 = 3.83 ppm, J,, = 10 Hz. Mass spectrum, amongst others, 610 (Parent), 266 (Michler's ethylene), 344 ( P -266).