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• W2055299968 abstract "Für die cis-O,O,N-Tris-σ-homobenzole 1a,b wurden drei alternative Synthesen, letztlich ausgehend von Benzol oder p-Chinon, entwickelt. Für eines dieser Verfahren wurde die radikalische Bromierung von (Tosylimino)-1,4-cyclohexadien und die Äquilibrierung bzw. Trennung der daraus resultierenden Mono- bzw. Dibromide untersucht. Zwischenprodukte der Synthesen wurden für die Herstellung der trans-O,O,N-Tris-σ-homobenzole 6/7 verwendet. Der für die cis-O,N,N-Verbindung 2a entwickelte Zugang basiert auf cis-Benzoldioxid (11). cis-/trans-N,N,C- (3a, b/9a und cis-/trans-O,N,C-Tris-σ-homobenzole (5a, b/10a, b) wurden über CH2N2-Addition an cis-N,N- bzw. cis-N,O-Bis-σ-homobenzole zugänglich. Ein effizienter Zugang zu cis-N,N,C-Gerüsten (3) geht von gut zugänglichen cis-O,O,C-Verbindungen (51) aus. Letztere sind auch Edukte für cis-S,S,C-Tris-σ-homobenzole (4). Die cis-Tris-homobenzole 1a,b (1b: ΔH≠ = 37.1 ± 2.1 kcal/mol, ΔS≠ = 4.1 ± 4.4 e.u.), 2 (2a, ΔG≠ = 33.7 kcal/mol), 3a,b (3a: ΔG≠ = 28.6 kcal/mol; 3b: ΔH≠ = 29.5 ± 1.1 kcal/mol, ΔS≠ = −2.4 ± 2.7 e.u.) und 5a,b (5b: ΔG≠ = 30.2 kcal/mol) gehen die thermische [σ2 + σ2 + σ2]-Cycloreversion zu den jeweiligen O,N-Heteroninen ein. Die Aktivierungsbarrieren sind im Einklang mit einer kooperativen 3σ→3π-Isomerisierung. Für das 4,7-Dihydro-1,4,7-oxadiazonin 67a ist durch Röntgenstrukturanalyse eine verdrillte Bootkonformation ausgewiesen. cis-/trans-[1.1.1]-O,N,C,-Tris-σ-homobenzenes — Syntheses, [σ2 + σ + σ]cycloreversions, O, N-Heteronines For the cis-O,O,N-Tris-σ-homobenzenes 1a,b three alternative syntheses, ultimately starting from benzene of p-quinone, have been devised. In the course of one of these approaches the radical bromination of (tosylimino)-1,4-cyclohexadiene and the equilibration/separation of the resulting mono-/dibromides has been studied. Intermediates obtained in these routes are employed for the preparation of the trans-O,O,N-tris-σ-homobenzenes 6/7. For the cis-O,N,N compound 2a a preparatively useful route is based on cis-benzene dioxide (11). cis-/trans-N,N,C- (3a, b/9a) and cis-/trans-N,N,C- (3a, b/9a and cis-/trans-O,N,C-Tris-σ-homobenzenes (5a, b/10a, b) are prepared by CH2N2 addition to the cis-N,N-/N,O-bis-σ-homobenzenes. A high-yield access to cis-N,N,C systems (3) starts from well available cis-O,O,C compounds (51). From the latter a cis-S,S,C-tris-homobenzene (4) is built up also. The tris-σ-homobenzenes 1a, b (1b: ΔH≠ = 37.1 ± 2.1 kcal/mol, ΔS≠ = 4.1 ± 4.4 e.u.), 2 (2a, ΔG≠ = 33.7 kcal/mol), 3a,b (3a: ΔG≠ = 28.6 kcal/mol; 3b: ΔH≠ = 29.5 ± 1.1 kcal/mol, ΔS≠ = −2.4 ± 2.7 e.u.) und 5a,b (5b: ΔG≠ = 30.2 kcal/mol) and 5a, b (5b: ΔG≠ = 30.2 kcal/mol) undergo the thermal [σ2 + σ2 + σ2] cycloreversion to provide the corresponding O,N-heteronines. The activation barriers are in accord with expectations based on the cooperative 3σ→3π isomerization. The 4,7-dihydro-1,4,7-oxadiazonine 67a crystallizes in a distorted boat conformation (X-ray analysis)." @default.
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• W2055299968 title "<i>cis‐/trans</i> ‐[1.1.1]‐O,N,C‐Tris‐σ‐homobenzole — Synthesen, [ _σ 2 + _σ 2 + _σ 2]‐Cycloreversionen, O,N‐Heteronine" @default.
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• W2055299968 doi "https://doi.org/10.1002/cber.19881210423" @default.
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