Abstract
Both pyrophosphoryl chloride and phosphorus oxychloride react with aryl aliphatic acids to form mixed anhydrides which undergo intramolecular acylation to afford cyclic ketones without the addition of a Friedel-Crafts catalyst. Aryl and aroyl-benzoic acids could be cyclized to the corresponding anthrones and anthraquinones respectively.
Highlights
Intramolecular acylation of aryl aliphatic acids is an important route for the preparation of cyclic ketones
Shah used a combination of phosphorus oxychloride and zinc chloride to synthesize 4-hydroxycoumarins from phenols and malonic acid [6]
Cyclization by concentrated sulfuric acid is more prone to undesired side-reactions such as enolization and aromatic substitution. In view of these precedents, we sought to investigate the potential of pyrophosphoryl chloride and phosphorus oxychloride in effecting intramolecular acylation, hoping to overcome some of the shortcomings of other condensing reagents
Summary
Introduction: Intramolecular acylation of aryl aliphatic acids is an important route for the preparation of cyclic ketones. A very useful method for effecting such acylation is the Friedel-Crafts reaction that employs the acid chloride or anhydride in the presence of catalysts like aluminum chloride or stannic chloride. In view of these precedents, we sought to investigate the potential of pyrophosphoryl chloride and phosphorus oxychloride in effecting intramolecular acylation, hoping to overcome some of the shortcomings of other condensing reagents.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
