Journal
TETRAHEDRON LETTERS
Volume 57, Issue 3, Pages 325-328Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.12.009
Keywords
Substituent effects; Triphenylphosphine; Iodine; Anhydrides; Amides
Categories
Funding
- Thailand Research Fund through the Royal Golden Jubilee Ph.D. Program [PHD/0206/2556, PHD/0086/2557]
- Center of Excellence for Innovation in Chemistry (PERCH-CIC), Chiang Mai University, Thailand
Ask authors/readers for more resources
The formation of acid anhydrides from the phosphorous-mediated activation of carboxylic acids was investigated. Under various systems, activation of benzoic acid in the presence of base led to the formation of benzoic anhydride at different rates depending on the reactivity of the reagents. Using the Ph3P-I-2/Et3N combination, most aryl acids were converted into the corresponding anhydrides in high yields within 5-10 min. However, for nitro-substituted derivatives, unexpectedly, N,N-diethylamides were isolated without anhydride formation. These results indicated the pronounced effect of substituents in governing these potential side reactions which can significantly affect the yields of acylation reactions promoted by phosphonium species. (C) 2015 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available