Tetrahedron p. 13919 - 13932 (1996)
Update date:2022-08-03
Topics:
Saito, Seiki
Kuroda, Akiyoshi
Matsunaga, Hiroshi
Ikeda, Shushiro
A plausible mechanism has been proposed for the exclusive formation of symmetrical dienediol such as 1,6-bis(acetoxy)-2,4-diene in palladium(II)-promoted [3,3]sigmatropic rearrangement of 3,4-bis(acetoxy)-1,5-diene system. This mechanism referred to as migration-induced intramolecular dioxanium ion switching (MIDIS) process can reasonably explain why the vicinal acetoxy groups move from 3,4-position and not to 5,6- but two directionally to 1,6-position.
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(1996)
