ad.infinitum - 22-11-2013 at 00:59
If left to stand in acid (a guess for suitable acid would be acetic acid), would methylenecyclohexane rearrange to give methlycyclohex-1-ene?
My thought being that the most substituted double bond would be more favorable thermodynamically. I have attempted the reaction mechanism and it seems
possible (since an acid will reversibly allow conversion between the two)
Thanks in advance for any responses
Dany - 22-11-2013 at 05:17
Yes this is totally feasible. It has been tried with species that act like Lewis acid (SO2) see [1]. Also the isomerization of olefin to
the more thermodynamically stable isomer has been described with ammonium hypophosphite NH4H2PO2 see [2]
Dany.
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ad.infinitum - 22-11-2013 at 08:18
Thanks for the info! Looks like a lewis acid is a better way to go from the research, I would like to give it a go with glacial AcOH at some point
though.