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Last updated at November 25th, 2020The Parikh–Doering oxidation is an oxidation reaction that transforms primary and secondary alcohols into aldehydes and ketones, respectively. The procedure uses dimethyl sulfoxide (DMSO) as the oxidant, activated by the sulfur trioxide pyridine complex in the presence of triethylamine base.
Status : OnlineParikh–Doering oxidation of alcohol 132 and Wittig reaction furnished the vinyl epoxide, which was treated with tetra-n-butylammonium fluoride (TBAF) to give 133. The second 6-endo epoxide cyclization with PPTS led to the formation of ring-G in 92% yield.
Status : OnlineThe Parikh-Doering oxidation uses SO 3 •Py (a solid reagent that can be handled easily) as the activator of DMSO. This reaction is especially effective for the oxidation of allylic and secondary alcohols. Unlike the Swern reaction, the reaction works at room temperature and is less prone to the methylthiomethyl ether byproduct formation. ...
Status : OnlineA Parikh-Doering oxidation is preferred over a Swern oxidation on a big scale, because the former can be carried out under non-cryogenic temperatures, the reagents are easier to handle, and there is a greater flexibility to add more reagent if the reaction does not proceed to completion.
Status : OnlineThis reaction is to oxidize primary and secondary alcohols into aldehydes and ketones at room temperature using sulfur trioxide‐pyridine complex in combination with dimethylsulfoxide and triethylamine and is called the Parikh–Doering oxidation. All the features of this reaction have been discussed.
Status : OnlineDMSO – Pyridine-SO 3 (Parikh-Doering) DMSO – Pyridine-SO 3 (Parikh-Doering) Mechanism + Description. This widely used Swern variant uses pyridine-sulfur trioxide complex as an activating agent in a mechanism analogous to the Swern and Pfitzner-Moffat mechanisms. General comments.
Status : OnlineDie Parikh-Doering-Oxidation ist eine Namensreaktion in der organischen Chemie, die nach ihren Entdeckern Jekishan R. Parikh und William v. E. Doering benannt wurde.. Mit der Parikh-Doering-Oxidation werden primäre und sekundäre Alkohole in Aldehyde beziehungsweise Ketone überführt. Hierbei wird wie bei der Swern-Oxidation aktiviertes Dimethylsulfoxid (DMSO) als Oxidationsmittel eingesetzt.
Status : OnlineParikh-Doering oxidation protocols (Fig.3) [6, 7, 10], and the activated intermediate ("active DMSO" species): N-succinimide ether of dimethyl sulfoxide (N-succinimide dimethyl sulfoxide ether, dimethyl sulfoxonium N-succinimidate), which can be prepared from dimethyl sulfide and N-chlorosuccinimide (NCS) or N-bromosuccinimide, and that
Status : OnlineThe initial intermediate for the Parikh–Doering is Me2SOSO3, where sulfate is the leaving group and there is pyridine hanging around to, like you said, possibly stabilize something. Apparently, when this is warmed up the sulfate doesn't eliminate like the chloride does. It sits around and waits for an alcohol to do SN2 at the sulfur.
Status : Online概要 取用容易的固体、SO3・Py与DMSO的协同作用下发生的氧化反应。 能够将烯丙醇氧化以及氧化叔醇。 与Swern氧化反应不同的是、室温下就能发生氧化反应。会产生二甲基硫醚的副反应不易发生。 基本文献 ・ Parikh, J.P.; Doering, W.E.J. Am. Chem. Soc. 1967, 89, 5505. DOI: 10.1021/ja00997a067 ・ Revi…
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