The synthesis of bis(propynoyloxy) aromatics

Abstract

Ten ble(propynoyloxy) aromatice were prepared, In yields ranging from 28% to 88%, from propynoyl chloride and the dleodlum salt of the corresponding dlhydroxy aromatic. The structures of these ethynyl compounds were confirmed by IR, 1H NMR, and DSC.Ethynyl groups have received much attention as a function capable of thermal chain extension and cross-linking by an addition process. Many ethynyl or acetylene-terminated (AT) aromatic systems show promise for uses in composite applications because they have been shown or proposed to form highly cross-linked matrices when heated above 200 °C (1-6).

Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2H-Chromenes

“…The only notable failure involved efforts to prepare the mono-propiolate ester of hydroquinone ( 44 ) (see entries 32 and 46, Table ), although modest quantities (23%) of the corresponding and previously reported bis-ester 99 (see entry 45, Table ) could be obtained. The spectral data acquired on all the product esters were completely consistent with the assigned structures.…”

“…Compound 99 (90 mg, 23%) ( R f = 0.6 in chloroform) was prepared using General Procedure B and isolated as a colorless, crystalline solid, mp 158–159 °C (lit . mp 159 °C).…”