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

✍ Scribed by Norbert De Kimpe; Roland Verhé; Laurent De Buyck; Niceas Schamp

• Book ID: 102773260
• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 642 KB
• Volume: 84
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19750840502

✦ Synopsis

Abstract

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.