Structure of a diazecine derivative from the condensation of phthaloyl chloride with ethylenediamine

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Abstract
The high dilution condensation of phthaloyl chloride with ethylenediamine has afforded not the benzodiazocine derivative 14, as reported earlier, but a more complex compound (17) which has been found to be a bridged dibenzodiazecine derivative. Treatment of 17 with ethanol causes alcoholysis of two of the four bridgehead lactam linkages. On heating, 17 isomerizes by a double ring → chain rearrangement to 1,2-diphthalimidoethane. The n.m.r. spectrum of 17 is discussed in terms of three possible conformations of the ten-membered ring.

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