1793-97-1Relevant academic research and scientific papers
An Intramolecular Iodine-Catalyzed C(sp3)?H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans
Br?se, Stefan,Koch, Vanessa
supporting information, p. 3478 - 3483 (2021/07/22)
The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C?H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)?H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.
DEPLACEMENTS HOMOLYTIQUES INTRAMOLECULAIRES . 12 - DECOMPOSITION INDUITE DE PEROXYDES ETHYLENIQUES : INFLUENCE DE LA LONGUEUR DE LA CHAINE
Bourgeois, M. J.,Maillard, B.,Montaudon, E.
, p. 5309 - 5320 (2007/10/02)
Products analyses of the thermolyses of the peroxides CH2=CH-(CH2)nOOtBu, 1, (n=1-5) showed that an induced decomposition of 1 occurred for n=1,2,3,4.Free radical additions of THF, carbon tetrachloride, bromotrichloromethane to 1 have been performed at lower temperature; they allowed, through the isolation of an adduct peroxide, at least in one case for each peroxide, to prove that a two-steps mechanism (addition of radical Z. to the double bond, intramolecular homolytic displacement) is involved in the induced decomposition of 1.The order of magnitude of the rate constants of these SHi reactions could be estimated.
