1197-67-7Relevant academic research and scientific papers
An easy method for the generation of amides from ketones by a Beckmann type rearrangement mediated by microwave
Eshghi, Hossein,Gordi, Zinat
, p. 2971 - 2978 (2007/10/03)
A facile and efficient procedure is developed for one-pot synthesis of amides from ketones in the presence of P2O5/SiO 2 reagent in dry media under microwave irradiation. Ketoximes indirectly in the same conditions gave amides by Beckmann rearrangement.
Schmidt reaction on camphor. Part I. Structure of the products
Hunter, Norman R.,Khan, M. Zafar,Marat, Kirk,El-Kabbani, Ossama A. L.,Delbaere, Louis T. J.
, p. 137 - 149 (2007/10/02)
A reinvestigation of the major product from the Schmidt reaction on camphor has led to the assignment of the structure as 1,9,9-trimethyl-3-oxo-2,8-diazabicyclononane (5).The structure has been established by high-field proton and carbon-13 nuclear magnetic resonance, as well as degradation to the imine ester 4.Confirmation of the structure of 5 was achieved by X-ray crystallography.Compound 5, C10H18N2O, crystallized in space group P21/a with a = 14.934(1) Angstroem, b = 10.973(1) Angstroem, c = 12.341(1) Angstroem, β = 92.0 deg, and Z = 8.The relatively rare cis amide linkage is present in the molecule.In addition to the amino amide 5, the Schmidt reaction on camphor leads to small amounts of the tetrazole 8 and the imine nitrile 9.
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).
Unusual regiochemistry in a beckmann-like rearrangement of camphor. α-Camphidone via methylene migration.
Krow, Grant R.,Szczepanski, Steven
, p. 4593 - 4596 (2007/10/02)
Reaction of camphor with hydroxylamine-O-sulfonic acid affords the nitrogen insertion product α-camphidone by migration of the methylene group rather than the bridgehead. Since Beckmann rearrangements of trigonal oximes afford bridgehead cleavage products with camphor, an alternative synchronous rearrangement of a tetrahedral intermediate is proposed for this Beckmann-like reaction.
