Cyclobutylmethyl

It has been found empirically that central analgesics that possess some degree of activity as antagonists of the effects of morphine tend to show a reduced propensity for causing physical addiction. Again empirically, it was noted that this could often be achieved by replacement of the N-methyl group by allyl, cyclopropylmethyl, or cyclobutylmethyl additional nuclear modifications often contributed to this activity. 

Chemical Name N-cyclobutylmethyl-14-hydroxydihydronormorphinone Common Name —... 

The dicyclobutanecarbonyl derivative (136.7 g) was dissolved in 200 ml of tetrahydrofuran and added dropwise to a suspension of 34.2 g of lithium aluminum hydride in 1 liters of tetrahydrofuran. The temperature of the mixture rose to reflux during the addition. Reflux was maintained for 2 hours after the addition was completed. After cooling, 110 ml of ethyl acetate was added dropwise, followed by 30 ml of water, followed by a solution of 53 g of ammonium chloride in 125 ml of water. The resulting mixture was filtered and the inorganic precipitate was washed with methanol. Evaporation of the combined filtrates gave 66 g of N-cyclobutYlmethyl-14-hYdroxydihydronormorphinone, melting point 229 to 231 . ... 

An experimental and calculational NMR investigation of dicyclopropyl substituted cyclobutylmethyl cation (19)45 has shown that IGLO/DZ//B3LYP/6-31G(d) calculated 13C NMR chemical shifts facilitate the assignment of the spectra. 

Chapter 5 by M. Fujita and T. Okuyama examines the ringopening reactions of alkylidenecyclopropanone acetals for solvolytic generation and trapping of alkylideneallyl cations (resonance hybrids of 1-vinyl-substituted vinyl cations). In Chapter 6 by V. P. Reddy et al. stable ion and computational studies of cyclobutylmethyl cations are discussed. In Chapter 7, G. I. Borodkin and V. G. Shubin discuss and... 

Figure 2. Product distribution from the solvolysis of nopinyl brosylate, a cyclobutylmethyl substrate.

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