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- W2042964075 abstract "Mit jeweils gut zugänglichen Ausgangsmaterialien (11, 25) werden zwei Synthesen für das cis-Oxaaza-bis-σ-homobenzol-Gerüst entwickelt. Die erwartungsgemäß isolierbaren N-SO2R-Derivate 3a, b gehen beim Erwärmen rasch und einheitlich die [π2 + σ2 + σ2]-Cycloreversion in die 4H-1,4-Oxazocine 6a, b ein (3b: t1/2 (60°C) = 33.2 min; ΔG≠ = 104.0kJ. mol−1). Letztere bevorzugen eine nicht-planare, gefaltete Konformation. Ausgehend von einem Synthesezwischenprodukt (27a) wird in zwei Varianten und in jeweils sehr geringer Ausbeute (2–6%) auch das thermisch beständige trans-Oxaaza-bis-β-homobenzol 9 hergestellt. cis,trans-Oxaaza-bis-σ-homobenzenes – 4H-1,4-Oxazocines The cis-oxaaza-bis-σ-homobenzene framework has been synthesised via two routes starting from readily accessible materials (11, 25). As expected the N-SO2R derivatives 3a, b are sufficiently stable to be isolated; on heating, they readily and quantitatively undergo [π2 + σ2 + σ2]-cycloreversion to the 4H-1,4-oxazocines 6a, b (3b: t1/2 (60°C) = 33.2 min; ΔG≠ = 104.0 kJ·mol−1). The latter prefer a non-planar, folded conformation. Using a precursor of 3b (27a), the thermally stable trans-oxaaza-bis-σ-homobenzene 9 was obtained in very small yield (2–6%) by two alternative pathways." @default.
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- W2042964075 date "1983-07-01" @default.
- W2042964075 modified "2023-10-09" @default.
- W2042964075 title "<i>cis,trans</i> ‐Oxaaza‐bis‐σ‐homobenzole – 4 <i>H</i> ‐1,4‐Oxazocine" @default.
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- W2042964075 doi "https://doi.org/10.1002/cber.19831160711" @default.
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