Nitrosohydrazine conformations. The effect of replacing C (1)-H of 2-nitroso-2-azabicyclo [2.2. 2] octane derivatives by nitrogen

SF Nelsen, PM Gannett, DJ Steffek

Index: Nelsen, Stephen F.; Gannett, Peter M.; Steffek, Daniel J. Journal of Organic Chemistry, 1980 , vol. 45, # 19 p. 3857 - 3860

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Citation Number: 5

Abstract

Results We used the methodology of Seebach, 2 LDA deprotonation of the nitrosamine followed by reaction with methyl iodide, to prepare 2 and 3 from I. As expected from previous work, 2e no methylation occurs at C (l), because the C (1)-H bond is protected against deprotonation by being held near to the nodal plane of the NNO group. Similar methylations allowed preparation of the nitrosohydrazines 5 and 6 from 4. Minor improvements in the ...