- The synthesis of the N-ethoxycarbonyl derivative of 5-azabicyclo[2.1.0]-pent-2-ene (Dewar pyrrole) - The first member of the parent ring-system
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N-Ethoxycarbonyl Dewar pyrrole 9, the first member of the parent ring, is formed via photofragmentation of 6 at -60°C and trapped as its adduct with 1,3-diphenylisobenzofuran 11; above this temperature, 9 is unstable and isomerises to N-ethoxycarbonylpyrrole 10.
- Warrener, Ronald N.,Amarasekara, Ananda S.,Russell, Richard A.
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p. 1519 - 1520
(2007/10/03)
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- The Chemistry of Acyl- and Sulphonyl-thionitroso Compounds
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Thiophene S,N-ylides undergo cycloadditions with nucleophilic alkenes to give adducts with concomitant extrusion of acylthionitroso compounds.These new and highly reactive species may be trapped by dienes (to give thiazines by cycloaddition) or by enes (to give acylthiohydroxylamines by ene reaction).With suitable dienes such as isopropene and dimethylbutadiene, the ene reaction competes with the diene addition.In the absence of trap, ethyl thionitrosoformate in aromatic solvents yields bis(ethoxycarbonyl amino) sulphide, while with cyclopentadiene a 2:1 adduct, a rare example of a 1,3,2,4-dithiadiazine, is formed.Thiophene is shown to yield a transient S,N-ylide on treatment with ethoxycarbonylnitrene.
- Meth-Cohn, Otto,Vuuren, Gerda van
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p. 245 - 250
(2007/10/02)
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- ARE THIOPHENES ATTACKED AT SULPHUR BY NITRENES?
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Ethyl azidoformate is shown to attack a range of thiophenes at sulphur giving transient S,N-ylides which can be trapped with acenaphthylene as adducts; thiophene yields self-trapped products also.
- Meth-Cohn, Otto,Vuuren, Gerda van
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p. 1105 - 1108
(2007/10/02)
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