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Gansen, Petra

doi:10.1007/978-3-322-85106-2

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“…Darstellung der Oxadiazinone 1 l a [23], l b [l, 4, 241, l c [4], Id [l], l e [24], If [l]; lg, Darstellung wie fruher [4], aber die Ausbeuten lagen jetzt bei 6&8O% (fruher 54%), die Wellenzahl der IR-Bande im Bereich der Carbonylgruppen-Signale ist nicht 1754 [4], sondern 1772 cm-l; lh, Darstellung wie fruher [4], aber rnit hoherer Ausbeute (94% gegenuber 41%); l i [3], l k [l], 11 [3], l m 1101. (2-Propylf-2-phenyl-6H-1,.3,4-oxadiuzin-6-on (lj 2960, 2925, 2870), 1690, 1635, 1575, 1518, 1480, 1415, 1380, 1260, 1185, 1150, 1120, 1040, 920, 807, 780, 690.…”

Section: Beschreibung Der Versucheunclassified

“…10 ml wurden weitere 1.11 g (25%) farblose Kristalle erhalten, deren 'H-NMR-Spektrum (Tab. 1) das Vorliegen von 5a und (4a,4aa,5/3,8p)-4,4a,5,6,7,8-Hexahydro-3-oxo-1,4-diphenyl-5,8-methano-3H-2-benzopyran (12a) im Verhalt- 4-disubstituierten (4c~,4a~,5a,8ci)-4,4a,5,6,7,8-Hexahydro-3-oxo-5,8-methano-3H-2-benzopyranen (5 (exo, exo) -(3-(4-Nitrobenzoyl) bicyclo(2.2.ljhept-2-yl) (17), 150 (22), 118 (loo), 105 (24), 104 (15), 91 (15), nm (4.166, sh), 261 (4.281), 380 (2.904, sh). -'H-, 13C-NMR: Tab.…”

Section: Einige Reaktionen Des Y-oxoketens 4a Und Umsetzung Von Dipheunclassified

“…(exo,exo)- (5,5) [Mf], 368 (19), 366 (17) (33), 118 (loo), 105 (34), 92 (44), 91 (85), 56 (28). -UV (1 a, 4a,4ap,5a, 8a,8ap, 9a, 9ap, 1 ( 1 S*,2R*,3R',4R*,aS*)-(3-(4-Brombenzoyl) bicyclo Umsetzung der y-Oxoketene 4g,h,i rnit BF3.OEt2 in Gegenwart von Norbornen (1 a,4a,4ap,5a,8a,Sap,9a,9ap,1 Oa,l Oa p) -Tetradecah ydro-9- (4nitrophenyl)-l2-oxo-lO-phenyE-lO,9-(epoxymethano)-1,4:5,8 455 (12) [M+], 361 (30), 334 (24), 333 (loo), 305 (13), 105 (67), 77 (19), 67 (13), 66 (12).…”

Section: Darstellung Des Y-oxoketens 4d Aus 2-(4-bromphenyl)-5phenylomentioning

confidence: 99%

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Cycloadditionen von 6H-1,3,4-Oxadiazin-6-onen (4,5-Diaza-?-Pyronen). 14. Nicht katalysierte und durch Trifluoressigs�ure katalysierte Reaktionen von 6H-1,3,4-Oxadiazin-6-onen mit Norbornen

et al. 1995

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Cycloadditions of 6H‐1,3,4‐Oxadiazin‐6‐ones (4,5‐Diaza‐α‐pyrones). 14. Reactions of 6H‐1,3,4‐Oxadiazin‐6‐ones with Norbornene: Non‐catalysed and Catalysed by Trifluoroacetic Acid In 11 out of 13 non‐catalysed reactions of oxadiazinones 1 with norbornene, γ‐oxoketenes 4 were observed and could be isolated in three cases (4b,d,m). Except for 4m, all γ‐oxoketenes isomerised to enollactones of type 5 on thermolysis. However, 4b furnished the cyclobutene derivative 10 as the major product. No γ‐oxoketenes were detected in the reactions of 1k and 1l, which gave rise to the formation of 5k and the enollactone 19, respectively. The latter was converted into 5l on treatment with trifluoroacetic acid (TFA). Four oxadiazinones 1 were allowed to react with norbornene in the presence of TFA. Three of them (1a,b,l) afforded mixtures of enollactones of type 5 and their diastereomers 12. Heating of 4 in the presence of norbornene led to the formation of the symmetrical δ‐lactones 6. This process was observed to be efficient only where the conversion 4 → 5 is slow (4b) or inoperative (4m). In five cases, the treatment of the components with boron trifluoride etherate proved to be a useful preparative alternative (6a,d,g,h,m). On treatment of 4a with methanol, the pseudoester 7a was formed, whereas 4b gave mixtures of 7b and the esters 8b and 15. Hydrogen chloride converted 4b into the pseudochloride 14, which furnished pseudoester 7b on methanolysis. Reaction of 4b,m with formic acid gave rise to pseudoanhydrides of type 13. From 4b and TFA a mixture of the enollactones 5b and 12b was obtained. Boron trifluoride etherate transformed 4i to enollactone 12i; analogously, 12m resulted on treatment of 4m with trifluoromethanesulfonic acid.

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Section: Beschreibung Der Versucheunclassified

Section: Einige Reaktionen Des Y-oxoketens 4a Und Umsetzung Von Dipheunclassified

Section: Darstellung Des Y-oxoketens 4d Aus 2-(4-bromphenyl)-5phenylomentioning

confidence: 99%

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Cycloadditionen von 6H-1,3,4-Oxadiazin-6-onen (4,5-Diaza-?-Pyronen). 14. Nicht katalysierte und durch Trifluoressigs�ure katalysierte Reaktionen von 6H-1,3,4-Oxadiazin-6-onen mit Norbornen

et al. 1995

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Wirkung nach Plan

Cited by 1 publication

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Cycloadditionen von 6H-1,3,4-Oxadiazin-6-onen (4,5-Diaza-?-Pyronen). 14. Nicht katalysierte und durch Trifluoressigs�ure katalysierte Reaktionen von 6H-1,3,4-Oxadiazin-6-onen mit Norbornen

Cycloadditionen von 6H-1,3,4-Oxadiazin-6-onen (4,5-Diaza-?-Pyronen). 14. Nicht katalysierte und durch Trifluoressigs�ure katalysierte Reaktionen von 6H-1,3,4-Oxadiazin-6-onen mit Norbornen

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