408315-82-2Relevant academic research and scientific papers
Synthesis of naphthalenyl acetate by platinum-catalyzed [1,5]-sigmatropic hydrogen shift of propargylic esters
Shu, Xing-Zhong,Ji, Ke-Gong,Zhao, Shu-Chun,Zheng, Zhao-Jing,Chen, Jing,Lu, Li,Liu, Xue-Yuan,Liang, Yong-Min
experimental part, p. 10556 - 10559 (2009/12/03)
A study was conducted to demonstrate the synthesis of naphthjalenyl acetate by platinum-catalyzed [1,5]-sigmatropic hydrogen shift of propargylic esters. Optimization investigations of the synthesis started with propargylic ester, with various catalysts. It was demonstrated that platinum-promoted rearrangement of propargylic esters provides two isomers of allene complex. It was also demonstrated that the [1,5]-sigmatropic hydrogen shift product was isolated, when the methyl group was introduced in the benzyl position. It was observed that the configurational orientation of the acyloxy group away from the large substituents led to the formation of a platinum-coordinated six-membered ring opposite the R group, which prevented the H-shift process.
