Imidazolinylmethyl derivatives of a number of bicyclic and tricyclic ring systems were prepared and studied for their effect on experimental cardiac arrhythmias. One of the bicyclic compounds, 3-phenyl-2,3,4,5-tetrahydro-l-benzazepine, obtained by means of a Schmidt reaction on 2-phenyl-3,4-dihydro-l-naphthalenone fol-

carbonium character. However, conjagation of the carbonyl group with the developing double bond should, in terms of the E 2 mechanism, provide a strong driving force. This should be especially powerful in elimination from XX because conjugation of -zwith -CO-would be established in the transition state. Moreover, these reactions conform to the trans-stereoelectronic pattern characteristic of E 2 reactions [60,61]. [60] H. B. ilther and T. Reichstein, Helv. Chim. Acta 26, 492 (1943); E. Seebeck and T . Reichstein, ibid. 26, 536 (1943). [61] N.

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eight or ten such manipulations during 2-3 hr., the internal temperature could be raised to 132°where it was held without further incident for 30 min. The gray solid was collected, washed with water, and dried; it weighed 3.55 g., m.p. 203-207°( air). Recrystallization from ethyl' alcohol was accompanied by darkening of the solutions and consequent losses of material. However, by the judicious use of charcoal and filter aid the pure pyrrole IV was obtained, m.p. 223.2-224.3°, fa]n -58°, identical in spectra and analyses with that obtained from kryptogenin and methylammonium acetate.The aqueous filtrate from the reaction was treated with 250 ml. of 33% potassium hydroxide and extracted with ether. The washed and dried ethereal solution was evaporated, leaving 1.41 g. of crystalline material. This was the V-methylpyrrolidine V, crystallizing from ethyl acetate as needles, m.p. 214.0-215.2°(in vacuo), [