Preparation of Alkyl Ethers with Diallyltriazinedione‐Type Alkylating Agents (ATTACKs‐R) Under Acid Catalysis

Diallyltriazinedione‐type acid‐catalyzed alkylating agents (ATTACKs‐R) with 10 different alkyl groups (R), including benzyl, substituted benzyl, allyl, and methyl groups were synthesized. The palladium‐catalyzed intramolecular O ‐to‐ N allylic rearrangement of 2,4‐bis(allyloxy)‐6‐chloro‐1,3,5‐triazine was developed to introduce various alkoxy groups into the N , N′ ‐dialkylated triazinedione skeleton. O ‐Alkylation of alcohols with ATTACKs‐R was carried out in 1,4‐dioxane in the presence of 2,6‐di‐ tert ‐butylpyridinium trifluoromethanesulfonate or trifluoromethanesulfonic acid as a catalyst. Six selected ATTACKs‐R bearing benzylic R groups were employed to prepare alkyl ethers from primary, secondary, and tertiary alcohols. The reactions of ATTACKs‐R bearing an o ‐nitro‐substituted benzyl group tended to afford low yields. Comparison of four different triazinedione‐based benzylating reagents suggested that the N , N′ ‐substituents affected the reactivity.