26347-24-0Relevant academic research and scientific papers
O-Alkylation of 3-hydroxyisoxazoles predominates under Mitsunobu conditions
Chen, Lijia,Fletcher, Steven
, p. 1693 - 1696 (2014/03/21)
Regiochemical control in the functionalization of ambident nucleophiles is of particular interest in organic chemistry. Herein, we demonstrate that O-alkylation of ambident 3-hydroxyisoxazoles, which are heterocyclic bioisosteres of carboxylic acids, predominates under Mitsunobu conditions. In several cases, excellent O-regioselectivity (≥95%) was observed. It is noteworthy that reactions were complete within 15 min at room temperature. Furthermore, the conditions are compatible with a range of alcohols that cover all of the typical protecting groups for the 3-hydroxyisoxazole motif, providing milder, simpler and less hazardous protocols to those commonly followed in the literature.
Cycloadditions with Alkoxynitrile Oxides, RO-CN+-O-, (Alkyl Cyanate N-Oxides)
El-Seedi, Hesham R.,Jensen, Henrik M.,Kure, Niels,Thomsen, Ib,Torssell, Kurt B. G.
, p. 1004 - 1011 (2007/10/02)
Alkyl formhydroximates have been synthesized by reacting alkyl orthoesters with hydrogen sulfide followed by treatment of the alkyl thioformate formed with hydroxylamine.Chlorination of alkyl formhydroximates with N-chlorosuccinimide gives alkyl chlorofor
