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Bargellini reaction information


Bargellini reaction
Named after Guido Bargellini
Reaction type Coupling reaction

The Bargellini reaction is a chemical reaction discovered in 1906 by Italian chemist Guido Bargellini.[1] The original reaction was a mixture of the reagents phenol, chloroform, and acetone in the presence of a sodium hydroxide solution.[2] Prior to Bargellini's research, the product attributed to this multi-component reaction (MCR) had been described as a phenol derivative in chemistry texts at the time. However, Bargellini demonstrated that a carboxylic acid derivative was actually the correct structure.

Later, organic chemists have used the reaction as a general method of organic synthesis for highly hindered or bulky morpholinones or piperazinones from ketones (particularly acetone) and either β-amino alcohols or diamines.[3]

  1. ^ Papeo, Gianluca; Pulici, Maurizio (2013-09-04). "Italian Chemists' Contributions to Named Reactions in Organic Synthesis: An Historical Perspective". Molecules. 18 (9): 10870–10900. doi:10.3390/molecules180910870. PMC 6270118. PMID 24008246.
  2. ^ Bargellini, Guido (June 4, 1906). "Azione del cloroformio e idrato sodico sui fenoli in soluzione nell'acetone" [Action of chloroform and sodium hydroxide on phenols in acetone solution]. Gazzetta Chimica Italiana.
  3. ^ Serafini, Marta; Murgia, Ilaria; Giustiniano, Mariateresa; Pirali, Tracey; Tron, Gian Cesare (2021-01-21). "The 115 Years Old Multicomponent Bargellini Reaction: Perspectives and New Applications". Molecules. 26 (3): 558. doi:10.3390/molecules26030558. ISSN 1420-3049. PMC 7865529. PMID 33494521.

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