77803-77-1Relevant academic research and scientific papers
Hetero-Diels-Alder reaction of phosphinyl and phosphonyl nitroso alkenes with conjugated dienes: An aza-Cope rearrangement
De Los Santos, Jesus M.,Ignacio, Roberto,Rubiales, Gloria,Aparicio, Domitila,Palacios, Francisco
experimental part, p. 6715 - 6725 (2011/10/09)
Phosphorylated nitroso alkenes react with cyclic dienes such as cyclopentadiene or cyclohexadiene to afford hetero Diels-Alder-type cycloadducts where the nitroso alkene participates as dienophile component and the cyclic olefin acts as the 4π-electron (diene) system. Subsequent aza-Cope rearrangement affords highly functionalized 5,6-dihydro-4H-1,2-oxazines. Conversely, the reaction of TMS-substituted cyclopentadiene (dienophile) with nitroso alkenes as heterodienes leads directly to bicyclic 1,2-oxazines. Theoretical studies are in agreement with the experimental results and with the new aza-Cope rearrangement proposed.
THE MICROBIAL REDUCTIVE SPLITTING OF THE N-O BOND OF DIHYDROOXAZINES; AN ALTERNATIVE TO THE CHEMICAL REDUCTION
Klier, K.,Kresze, G.,Werbitzky, O.,Simon, H.
, p. 2677 - 2680 (2007/10/02)
In the presence of artificial mediators many bacteria reductively split the N-O bond of dihydrooxazines in a chemoselective way if hydrogen is used as an electron source.The yields as determined by HPLC are almost quantitative i.e. considerably better tha
Polyhydroxyamino Compounds via Diene Synthesis with Nitroso Compounds, IV. - Preparation and Stereochemistry of Dideoxyinosamine Derivatives
Kresze, Guenter,Kysela, Ernst
, p. 202 - 209 (2007/10/02)
The general method for the synthesis of polyhydroxy amines by Diels-Alder reactions with a nitroso compound, reduction of the adduct with cleavage of the N - O bond and hydroxylation of the remaining C = C -double bond, can also be realized with α-chloronitrosocyclohexane as dienophile, in good yield.Primary amines are synthesized in this way.
