Reactivity of α,α‐Dihalogeno‐Imino Compounds Part VII: Reactivity of N‐1‐(2,2‐dichloroalkylidene)t. Butylamines

Treatment of N‐1‐(2, 2‐dichloroalkylidene)t.butylamines 1a‐c with excess methanolic sodium methoxide under reflux afforded mainly a mixture of α‐methoxy‐α,β‐unsaturated aldimines 2a‐c and the rearrangement products 3, besides small amounts of N‐t.butyl 2‐chloroamides 4 and N‐t.butyl 2‐chloro imidates 6. On the other hand, N‐1‐(2, 2‐dichlorobutylidene)t.butylamines 1d‐e gave α‐chlo‐ro‐α, β‐unsaturated aldimines, while α, α‐dichloropropylidene t.butylamine 9 provided mainly the α‐methoxy‐α,β‐unsaturated aldimine 11 next to the α‐me‐thoxyamide 12, α, α‐dimethoxyaldimine 10 and the rearrangement product 13. The reaction mechanisms are discussed.