REACTION OF DIMETHYLETHYLIDENECARBENE WITH OLEFINS

Treatment of 5,5-dialkyl-N-nitrosooxazolidones with lithium alkoxides in the presence of olefins affords disubstituted methylenecyclopropanes. The relative rates of reaction of the intermediate, dimethylethylidenecarbene,2 with styrenes indicate that the olefins act as nucleophiles (ρ = –3.4 for p-CH3, p-H, p-Cl). However, since tetramethylethylene reacts much less rapidly than cyclohexene, a steric effect is operative. A possible steric course for the addition reactions is outlined. © 1969, American Chemical Society. All rights reserved.