Sigmatropic [3,3] rearrangements of N-allyleneamines are known as aza-Claisen rearrangements. This reaction is analogous to the Claisen rearrangement of allyl vinyl ethers.

aza claisen 01

The reaction goes under milder conditions if the nitrogen is charged (ammonium salt)

aza claisen 02

The aza-Claisen reaction is a concerted process that proceeds through a six-membered transition state that assumes a chair arrangement with the substituents arranged nearly equatorially.

aza claisen 03