Sciencemadness Discussion Board

Nitrosation on Meyers modification reaction

IanCaio - 7-10-2012 at 11:05

Hey guys,

I've been reading about nitrification of organic substracts, and on the Meyers modification reaction, it says that you should worry about the Nitrosation that happens as a side reaction:

(in presence of NO2-)
RR'CHNO2 + RR'CHONO2 -> RR'CHOH + RR'C(NO)NO2

Im just wondering if this reaction only happens if you are reacting secondary akyl halides, since it would form the secondaries nitroalkanes and nitrite esters as the ones in the reaction, or if it also happens on primary alkyl halides, and if so, how it would happen? Would that be the reaction?

(in presence of NO2-)
RCH2NO2 + RCH2ONO2 -> RCH2OH + RCH(NO)NO2

What I understood from the book is that there would be nitrosation even with primary alkyl halides reactions, but wouldn't there be any carbocation rearrangement? I'm finding hard to assume anything because I'm not sure of the reaction mechanism..

IanCaio - 10-10-2012 at 11:52

Not even a clue?

If thats something too specific you can tell me. At least I would lower my hopes on getting an answer. Maybe its not some important information for the overall idea of the book. Im just trying to learn about energetic materials :)
By the way, the book I'm reading is the "Organic Chemistry of Explosives" by Jai Prakash