96093-87-7Relevant 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
ASYMMETRIC DIELS - ALDER REACTIONS WITH α-CHLORONITROSO COMPOUNDS - I. APPLICATION OF α-CHLORONITROSO EPIANDROSTERONE IN SYNTHESIS
Sabuni, Mahmud,Kresze, Guenter,Braun, Heinz
, p. 5377 - 5380 (2007/10/02)
The Diels - Alder reaction of 1,3-cyclohexadiene (9) with the enantiomerically pure α-chloronitroso compound 8, synthesized from epiandrosterone (7a), gives the adduct 10a with 1-(R),4-(S) configuration in 69 percent chemical yield and >=95 percent enantiomeric excess.
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.
