Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 52, 2022 - Issue 24
118
Views
0
CrossRef citations to date
0
Altmetric
Articles

Reaction of 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-dione with some phosphorus halides: A simple synthesis of novel 1,2-benzoxaphosphinines

, &
Pages 2334-2343 | Received 27 May 2022, Published online: 17 Nov 2022
 

Abstract

A simple method for design of some novel 1,2-benzoxaphosphinines 29, was achieved. The methodology depended on cyclization of 1-(2-hydroxy-phenyl)-3-phenylpropane-1,3-dione (1) as starting material with some phosphorus halides in dry solvent in the presence of a base. Reaction of the substrate 1 with some phosphorus halides, such as P,P-dichlorophenylphosphine, phenyl phosphonic dichloride, phenyl phosphorodichloridate, and phosphorus oxychloride in dry toluene containing triethylamine led to a predominant formation of 3-benzoyl-4-hydroxy-2H-1,2-benzoxaphosphinines 25, respectively. Under the same reaction conditions, the molecular structures of type 3-benzoyl-4H-1,2-benzoxaphosphinin-4-ones 6 and 7 were isolated by treatment of the substrate 1 with phosphorus pentachloride and phosphorus tribromide, respectively. In addition, the interesting 4-(1-phenyl-ethanoyl)-1,2,λ5-benzoxaphosphinines 8 and 9 were obtained by treatment of compound 1 with acetonyl and benzyl triphenylphosphonium chlorides, respectively, in dry dioxane and sodium hydride. The chemical structures of the title compounds were established by elemental analysis and spectral tools.

Graphical Abstract

Acknowledgments

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through large research groups program under grant number RGP.2/8/43.

Additional information

Funding

This work was supported by Deanship of Scientific Research at King Khalid University.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.