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A nitrogen-containing terpene 6,6-dimethyl-2-azaspiro[4.4]non-1-ene (polyzonimine) was isolated from the defensive secretion of the milliped Polyzonium rosalbum. Polyzonimine, which is repellent to such natural enemies of the milliped as ants, acts as a topical irritant to insects (10-4 M induces scratching in cockroaches). Its structure was confirmed by a five-step synthesis starting from 2,2-dimethyl-7-oxabicyclo[4.1.0]heptane.

Photoaddition of 2-(/3-Naphthyl)azirine with Acrylonitrile. Irradiation of a mixture of 2-(fi-naphthyl)azirine and acrylonitrile in benzene for 4 hr using a Pyrex filter gave 2-(d-naphthyl)-4-cyano-A'-pyrroline (37) as a crystalline solid (76%). This material was purified by thick layer chromatography using a mixture of 1:1 hexane-ethyl acetate as the eluent and was sublimed at 140°(0.01 mm) to afford an analytical sample, mp 143-144°; ir (KBr) 4.45,

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