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Beilstein J. Org. Chem. 2016, 12, 1590–1597, doi:10.3762/bjoc.12.155
Graphical Abstract
Figure 1: Relative stability and nucleophilicity of non-stabilized (R = H, alkyl) diazo compounds (left) and ...
Scheme 1: Synthesis of ethyl halodiazoacetates [11].
Figure 2: a) The decay of 2b in toluene-d8 at 35 °C. b) The plot of log(Δ[2b]) vs time.
Scheme 2: Proposed rate determining step for the thermal decomposition of 2a–c.
Figure 3: Transition-state energies (kcal/mol) for the release of N2 and formation of the singlet carbenes. T...
Figure 4: Thermal stability of 1 and 2a–c, and the α-substituents’ contribution to π-donation.
Figure 5: NBO atomic charges and IR stretching frequencies calculated [21] and experimentally recorded for 1 and ...
Figure 6: NBO atomic charges of the singlet carbenes from 1 and 2a,b, and d.
Figure 7: Relative thermal stability of halodiazoacetates (red color).
Figure 8: Relative nucleophilicity of halodiazoacetates (red color).
Beilstein J. Org. Chem. 2015, 11, 1944–1949, doi:10.3762/bjoc.11.210
Scheme 1: Synthesis of halo diazoacetates [17].
Scheme 2: The reaction between halodiazoacetates and indole.
Scheme 3: Proposed reaction pathway.
Scheme 4: Attempted cyclopropanation of N-Boc indole.
Scheme 5: The reaction between ethyl bromo diazoacetate and N-Me-indole.