79645-28-6Relevant academic research and scientific papers
Intramolecular Hydrogen Abstraction. (Diacetoxyiodo)benzene, a Useful Reagent for the Remote Functionalization of Non-Activated Carbon Atoms
Dorta, Rosa L.,Francisco, Cosme G.,Hernandez, Rosendo,Salazar, Jose A.,Suarez, Ernesto
, p. 1836 - 1854 (2007/10/02)
Photolysis with visible light of several hydroxy compounds such as (-)-6,6-dimethylbicycloheptan-2β-ol (1), 2-ethoxycarbonylmethyl-6,6-dimethylbicycloheptan-2β-ol (2), cedrol (5), isolongifolol (8), the hydrindane derivative (12), labdane-8α,15-diol (18), methyl 8α-hydroxylabdan-15-oate (19), labdanolic acid (20), methyl 3β-hydroxyfriedelan-29-oate (27), and friedelane-3β,30-diol 30-acetate (30) in the presence of (diacetoxyiodo)benzene and iodine leads to alkoxyl radicals which undergo intramolecular abstraction of suitably positioned hydrogen atoms to produce γ-functionalized derivatives.
Camphor/Longicamphor and 7β-Formylnorlongifolane/7β-Acetylnorlongifolane Oximes: A Comparative Beckmann Rearrangement Study
Satyanarayana, N.,Shitole, H. R.,Nayak, U. R.
, p. 997 - 1001 (2007/10/02)
Camphor oxime (3)/longicamphor oxime (4) have been shown to undergo Beckmann fragmentation on exposure to tosyl chloride in pyridine generating olefinic nitriles: 3->5+6 and 4->7+8+9; in the case of 4 this reaction provides an entry into the bicyclononane system characteristic of the secolongifolene diol fungal metabolite (10). 7β-Formylnorlongifolane oxime (14)/7β-acetylnorlongifolane oxime (15) when treated with the same Beckmann catalyst under similar conditions, afford the nitrile (16)/amide (17); on hydrolysis with base 17 gives the amine 18.Reaction of longicamphor (2) with hydroxylamine-O-sulfonic acid, however, a ffords the nitrogen-insertion product, α-longicamphidone (24) besides the fragmented nitrile (7).
