The stereochemistry of some carboxylic acids derived from 2-norbornene* and bicyclo[2,2,2]oct-2-ene was investigated.The reaction of either 5-e»docyano-2-norbornene (la) or 5-exocyano-2-norbornene (lb) with methyl chloride in the presence of sodamide and liquid ammonia gave 5-eradocyano-5-exomethyl-2-norbornene (III). As a by-product of both reactions, there was obtained an amidine fraction which upon saponification gave 2-norbornene-5-exocarboxamide (II); II also could

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A number of derivatives of 1,3-diazaspiro[4.5] dec-l-enAne and 1,3-diaza~pir0[4.5]dec-2enAne were prepared by the interaction of appropriately Substituted 1-aminocyclohexanecarboxamidea and ethyl orthoformate. The structure of these spiroimidazolones was confirmed by chemical interconversions to known materiala and by examination of their ultraviolet and infrared spectra. Two compounds previously* reported to possess the spiroimidamlone structure appear to be the isomeric 1-formylaminocyclohexanecarbonitrilea XI1 and XIII.As part of a program directed toward the synthesis of central nervous system depressants we investigated a series of spiroimidazolones of types (6) We are indebted to Dr. W. S. Waring, Imperial Chemical Industries, Limited, Pharmaceutical Division, Alderley Park, Maccledield, Cheshire, Great Britain, for supplying a number of samplea for purposes of comparison and for communicating to us spectral data which corroborated our findings. NOVEMBEB 1961 SYNTHESU AND STBU-OF SPIBOIMIDUOLONES

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