1587735-85-0Relevant academic research and scientific papers
Electrophile-Mediated Reactions of Functionalized Propargylic Substrates
Urbanaite, Aurelija,Jonu?is, Mantas,Buk?naitiene, Rita,Balkaitis, Simonas,?ikotiene, Inga
, p. 7091 - 7113 (2015)
Metal-free halogen, chalcogen, or oxocarbenium ion mediated yne-carbonyl or yne-thioxo transformations of a range of N- and O-propargylic compounds have been studied. This investigation has led to the development of a mild, economic, and effective method for the synthesis of functionalized 4H-1,3-oxazines, 4H-1,3-thiazines, 4,5-dihydrothiazoles, and α-substituted enones. The structure of the propargylic substrate and the nature of electrophile influence both the outcome and regioselectivity of processes. Metal-free electrophile-mediated transformations of various N- and O-propargylic compounds have been studied. The scope and limitations of these reactions have been evaluated by using a broad range of substrates.
Rearrangements of propargylic esters can be induced by some electrophiles
Cikotiene, Inga
supporting information, p. 2260 - 2263 (2014/05/06)
An electrophile-induced rearrangement of propargylic esters without need of transition catalysis is possible. In particular, this observation provides a mild, economic, and effective method for the introduction of benzyl ether derivatives to access functionalized α,β-unsaturated ketones. Preliminary mechanistic studies suggest that this rearrangement undergoes an intramolecular 1,3-acyloxy shift.
