596-29-2Relevant articles and documents
FORMATION OF CARBENIUM IONS AND NAKED ANIONS BY THE PROTONATION OF PHTHALOPHENONE WITH A SUPER ACID.
Brandner,Dickert,Lehmann
, p. 740 - 745 (1987)
Two molecules of a strong acid such as CF//3SO//3H are necessary to cleave the lactone ring of phthalophenone. NMR and conductivity measurements reveal that the carboxylate group has to be protonated for this purpose followed by its solvation with an additional molecule of acid. But CF//3SO//3** minus which is simultaneously formed behaves as a naked anion in the solvent dichloromethane. CNDO-calculations indicate a strong interaction between the charged central carbon atom and the COOH group in o-HOOH(C//6H//4)C** plus (C//6H//5)//2 which is accompanied by an unusually large twisting of the phenyl rings.
Phthalide synthesis through dehydrogenated lactonization of the C(sp3)-H bond by photoredox catalysis
Cai, Shunyou,Cai, Zhixiong,Chen, Shanyi,Huang, Mingqiang,Lai, Qihong,Lin, Yulin,Liu, Chao,Liu, Hui
, p. 8212 - 8216 (2021/10/29)
A practical and efficient method is established for the direct oxidative lactonization of the C(sp3)-H bonds relying on visible-light-induced photoredox catalysis. This protocol expediently allows the delivery of diverse phthalides using oxygen as the sole terminal oxidant under metal-free conditions at room temperature. Notably, the choice of an appropriate hydrogen atom transfer (HAT) cocatalyst is revealed to be critical for the success of this process.
Visible responses under high pressure in crystals: phenolphthalein and its analogues with adjustable ring-opening threshold pressures
Deng, Xinyuan,Guo, Hongwei,Meng, Xiao,Wang, Kai,Zou, Bo,Ma, Yuguo
supporting information, p. 4663 - 4666 (2019/05/02)
The ring-opening reaction of phenolphthalein (PP) crystals under hydrostatic pressure provided by using a diamond anvil cell (DAC) is described in this paper for the first time. The color of the crystals changed into red from colorless visibly. The ring-opening threshold pressures could be adjusted by changing the substituent groups. Mechanochromic responses under hydrostatic pressure could also be achieved in polymer blends, which contributes to their practical applications.
Domino [Pd]-Catalysis: One-Pot Synthesis of Isobenzofuran-1(3H)-ones
Mahendar, Lodi,Satyanarayana, Gedu
, p. 7685 - 7691 (2016/09/09)
An efficient domino [Pd]-catalysis for the synthesis of isobenzofuran-1(3H)-ones is presented. The strategy shows broad substrate scope and is amenable to o-bromobenzyl tertiary/secondary/primary alcohols. Significantly, the method was applied to the synthesis of antiplatelet drug n-butyl phthalide and cytotoxic agonist 3a-[4′-methoxylbenzyl]-5,7-dimethoxyphthalide.
