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Beilstein J. Org. Chem. 2019, 15, 2603–2611, doi:10.3762/bjoc.15.253
Graphical Abstract
Scheme 1: Stable betaines I–IV.
Scheme 2: Reactions of N-triflyl-propiolamides 1 with N- and P-nucleophiles. Tf = SO2CF3.
Scheme 3: Synthesis of betaines 3 by a three-component reaction. N-triflylpropiolamides 1: R = Ph (a), 4-Cl-C6...
Figure 1: Phosphonium betaines 3 prepared. An E:Z ratio of 100:0 means that only the E-isomer was observed in...
Scheme 4: Unexpected synthesis of E-3o.
Scheme 5: Betaines 3 from propiolic acid chlorides.
Scheme 6: Two mechanistic scenarios for the formation of betaines 3.
Figure 2: Solid-state structure of E-3a (ORTEP plot), two symmetry-independent molecules in the triclinic uni...
Figure 3: Solid-state structure of E-3b·CH2Cl2 (ORTEP plot); CH2Cl2 solvate molecule not shown.
Figure 4: Solid-state structure of E-3e·H2O·CH2Cl2 (ORTEP plot). The CH2Cl2 solvate molecule is disordered. H...
Figure 5: Solid-state structure of Z-3e (ORTEP plot).
Scheme 7: Resonance structures describing the bonding in 1,2-oxaphospholes/1,5-betaines 8.