51134-38-4Relevant academic research and scientific papers
Preparation of 2-substituted naphth[2,3-d]oxazole-4,9-diones via a radical chain process
Rathelot, Pascal,Njoya, Yves,Maldonado, José,Crozet, Michel P.,Vanelle, Patrice
, p. 1075 - 1084 (2007/10/03)
A novel series of ethylenic naphth[2,3-d]oxazole-4,9-diones was synthesized via an S(RN)1 mechanism from the 2-chloromethylnaphth[2,3- d]oxazole-4,9-dione. This mechanism was confirmed by the inhibitory effects of the use of dark, bubbling oxygen, cupric chloride, p-dinitrobenzene and TEMPO.
UNSYMMETRICAL CONNECTIVE OLEFINATION BY KORNBLUM NITRO-SYNTHESIS : APPLICATIONS IN PHYTUBERIN CHEMISTRY
Crombie, Leslie,Roughley, Brian S.
, p. 3147 - 3156 (2007/10/02)
Kornblum unsymmetrical olefin synthesis employing radical-anion chain crossed-coupling (light catalysed) of a mono- and a gem-di-nitro-compound, followed by reductive NO2 removal, is examined in the context of a hindered olefin structure required for phytuberin synthesis.Whilst successful for a tetrasubstituted olefin model (for which a Witting approach failed), increasing substitution on the β-position of the mono-nitro component supressed the coupling reaction, presumably for steric reasons.An alternative coupling involving a bromonitrocyclohexane and a mononitroacetal caused symmetrical coupling of the mononitro-component in high yield, rather than a crossed reaction.Reductive elimination (using Na2S/DMF) from either rac.- or meso- 1,2-dinitro-1,2-diphenylethane leads to (E)-stilbene 98percent (E) > probably through a stabilised radical or anion.A convenient preparation of triphenylisoxazoline-N-oxide is reported.
