60277-96-5Relevant articles and documents
EPR support for the ketyl radical-anion "triggered" [3,3]-sigmatropic rearrangement
Enholm, Eric J.,Battiste, Merle A.,Gallagher, Maria,Moran, Kelley M.,Alberti, Angelo,Guerra, Maurizio,Macciantelli, Dante
, p. 6579 - 6581 (2002)
New physical evidence to support a ketyl radicalanion mechanism for the [3,3]-sigmatropic rearrangement is presented. With use of EPR spectroscopy, spectra are observed that can be attributed to 8, an acyl radical-anion species resulting from a [3,3]-rear
Rearrangement of α-hydroxy imines to α-amino ketones: Mechanistic aspects and synthetic applications
Compain,Gore,Vatele
, p. 6647 - 6664 (2007/10/03)
In refluxing diglyme, rearrangement of α-hydroxy imines bearing diversely substituted allyl groups or a 3-trimethylsilylpropargyl group on the α-carbon to the nitrogen afforded in good yields α-amino ketones. Migration of allyl or 3-trimethylsilylallyl groups occurred without allylic transposition in contrast to be 1-methylallyl group. In the 3 cases studied, the rearrangement of enantioenriched α-hydroxy imines took place with complete 1,2-chirality transfer. The rearrangement was applied to the preparation of (+)-1-benzyl-1-azaspiro[5.5]undecan-7-one, a precursor in the synthesis of (-)-perhydrohistrionicotoxin.
INVESTIGATION IN THE FIELD OF AMINES AND AMMONIUM COMPOUNDS. CLXVII. STEVENS REARRANGEMENT OF (2-OXOCYCLOHEXYL)(2-ALKENYL)DIMETHYLAMMONIUM HALIDES
Kocharyan, S. T.,Karapetyan, V. E.,Panosyan, G. A.,Babayan, A. T.
, p. 292 - 297 (2007/10/02)
(2-Oxocyclohexyl)(2-alkenyl)dimethylammonium halides enter into the Stevens rearrangement in ether under the influence of potassium hydroxide and form 2-dimethylamino-2-(2-alkenyl)-1-cyclohexanones.When heated at 100-180 deg C, the 3,2-rearrangement produ
