1,2-Cyclobutanecarboxylates synthesized using photoreaction and esterification

Abstract

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 1,2benzenedicarboxylates 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. References [1] Amjaour.