1,2-Cyclobutanecarboxylates Synthesized Using Photoreaction and Esterification

Presented During:

08/03/2020: 4:00 PM  - 5:00 PM 


2020: 70th ACA Annual Meeting

Session Type:


Presenting Author :

Houssein Amjaour  
University of North Dakota

Additional Author(s):

Zhihan Wang  
Micah Mabin  
Qianli R. Chu  

Abstract Body:

Esters are importance targets or intermediates in the synthesis of plasticizers, perfumes, flavor chemicals, cosmetics, fine chemicals, pharmaceuticals, and chiral auxiliaries. However, ophthalates, a group of 1,2-benzenedicarboxylates derived from petrochemicals, are being gradually replaced by phthalate-free plasticizers in many products due to health concerns.

Truxinates, a family of 1,2-cyclobutanecarboxylates found in many natural products, share the structural similarities with o-phthalates and may serve as nontoxic phthalate alternatives. In this poster presentation, we report the synthesis of a series of mono- and di-esters of a 1,2-cyclobutanecarboxylic acid (CBDA-4, Figure 1) from trans-cinnamic acid using [2+2] photocycloaddition and subsequent esterification. The structures of many 1,2-cyclobutanecarboxylates were successfully determined by single crystal X-ray diffraction. These esters show promising potential for use in wide-ranging applications. For example, the cyclobutane ring in some esters was thermally cleavable at high temperature, providing a method by which materials made from them could be easily recyclable.

[1] Amjaour. H, Z. Wang, Mabin. M and Q. R. Chu, Chem. Commun. 2019, 55, 214-217.
[2] Wang, Z.; Scheuring, M.; Mabin, M.; Shahni, R.; Wang, Z. D.; Ugrinov, A.; Butz, J.; Chu,
Q. R., ACS Sustainable Chem. Eng. 2020, 8, 8909-8917.
[3] B. Cornils and P. Lappe, "Dicarboxylic Acids, Aliphatic" in Ullmann's encyclopedia of
industrial chemistry, Wiley-VCH, Weinheim, 2014.

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