Iron-Promoted 1,5-Substitution (SN2′′) Reactions of Enyne Acetates and Oxiranes with Grignard Reagents.

Autor: Taç, Doğan, Aytaç, İsmet Arınç, Karatavuk, Ali Osman, Kuş, Melih, Ziyanak, Fırat, Artok, LevENt
Předmět:
Zdroj: Asian Journal of Organic Chemistry; Oct2017, Vol. 6 Issue 10, p1415-1420, 6p
Abstrakt: Acetate derivatives of 2-en-4-yne alcohols 1 and enyne oxiranes 4 regioselectively underwent 1,5-substitution (SN2′′) reactions with Grignard reagents in the presence of an iron compound to provide vinylallenes exclusively with the ( E)-configuration. An alkali salt was needed to avoid the hydride-promoted reductive 1,5-substitution pathway for 1, whereas no such additive was needed for the effective conversion of 4 into the desired alkylated or arylated vinylallene structure. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index