Photosensitized Oxidation of Furans. 20.¹ A Novel Thermal Rearrangement of Suitably Substituted Alkoxyfuran Endoperoxides via Neighboring-Group Mechanism:  Synthesis and Reactivity of the First Functionalized 2-Oxetanyl Hydroperoxides

Abstract

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Rearrangements of organic peroxides and related processes

“…The rearrangement of endoperoxides 541a–c containing a substituent with a tertiary hydroxy group in the 5 position results in the formation of hydroperoxyoxetanes 542a–c and trace amounts of Z -ketoesters 543a–c . Under the same conditions, the rearrangement of endoperoxide 541d containing a substituent with a secondary hydroxy group in the 5 position produces exclusively the Z -keto ester 543d [ 497 ].…”

Expedient One-Pot Synthesis of γ-hydroxybutenolides Starting from Baylis-Hillman Adducts: Lactonization, Isomerization, and Aerobic Oxidation of α-Methylene-γ-hydroxyester

“…In some cases, especially under the influence of DBU instead of K2CO3, we observed the formation of a trace amount of hydroperoxide 6a, 9 which was changed to 7a by treatment with PPh3 quantitatively (vide infra).…”

Furan Oxidations in Organic Synthesis: Recent Advances and Applications

“…One of the most studied processes has been the photosensitized oxidation with synglet oxygen [64]. One of the most studied processes has been the photosensitized oxidation with synglet oxygen [64].…”