The oxidation of N-methyl-N-5-hexenylhydroxylamine with mercuric oxide and the condensation between 5-hexenal and N-methylhydroxylamine afforded cis-S-methyl-3-oxa-2-azabicyclo[3.3.0~octane (2). Other bicyclic isoxazolidines have been synthesized by the condensation reaction employing unsaturated aldehydes and unsaturated ketones. The structures of these compounds were proved by hydrogenolysis and, in some cases, independent synthesis of the amino alcohols. The mechanism of the cyclization reactions are postulated as intramolecular 1,3-additions of an unsaturated nitrone intermediate. The scope of this preparative route t o fused bicyclic isoxazolidines is discussed in terms of reactivity, orientation, and stereochemistry.The pyrolysis of a mixture of the isomeric N-methyl- methyl-8-oxa-2-azabicyclo[3.3.Oloctane (Z), and wasa-pipecoline oxides produced, in addition to the pre-postulated as having arisen from an unsaturated dicted unsaturated hydroxylamine, an unexpected nitrone intermediate (1). The nitrone may have been bicyclic base. * This product was identified as Nproduced from N-inethyl-N-5-hexenylhydroxylan1ine( 1 ) A preliminary communication concerning a part of this work has ap-by an oxidation-reduction reaction. However, this peared-J A m Chem Sot, 81, 6334 (1959). This work was reported in unsaturated hydroxylamine was obtained in good p a r t : Abstracts, 137th National Meeting of the American Chemical Society.Cleveland, Ohio, April 1960, p. 8.5-0.( 2 ) A C Cope and N A LeRel, J A m Chrm S o c , 81, 4656 (I$lRO)

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Copolymers of methyl methacrylate with methyl and ethyl α‐hydroxymethylacrylate and with α‐hydroxymethylstyrene have been prepared with free‐radical initiators at temperatures below 80°C. At higher reaction temperatures or under extrusion conditions, alcohol was eliminated and the free hydroxyl content was greatly decreased. All evidence indicates the formation of six‐membered lactone groups in this post‐polymerization reaction: direct evidence for their formation is lacking, however, since neither infrared nor nuclear magnetic resonance spectra could be used to detect lactonization in this system. The loss of activity from 14C ester‐labeled methyl methacrylate copolymer on heating could be correlated with the extent of lactonization. The degree of lactonization is relatively less with copolymers containing higher amounts of hydroxymethyl groups. The resulting polymers exhibit higher heat distortion temperatures and decreased impact resistance when compared to poly(methyl methacrylate). Attempts were made to incorporate similar lactone structures by cyclocopolymerization with methyl methacrylate of α‐methacryloxymethylstyrene or ethyl α‐methacryloxymethylacrylate, but only crosslinked polymers or polymers with pendent unsaturation were found.