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- W2059639734 abstract "N-Methyltetrahydrocarbazole (1) reacts with ethyl 2-nitrosopropenoate and with 3-nitrosobut-3-en-2-one to give the fused oxazines (2) in good yields. These adducts, when heated in xylene, undergo retro-Diels–Alder reaction to give the starting carbazole and the nitroso-olefins, which are intercepted by indole. Thermolysis of the adduct (2a) in pentanol results in the formation of the oximinoketone (6) in good yield. α-Nitrosostyrene also forms an adduct (2c) with N-methyltetrahydrocarbazole, but gives in addition the nitrone (3) and a 2:1 adduct, which is assigned the structure (4). The oxazine (2c) failed to undergo the retro-Diels–Alder reaction when heated in xylene. Attempts to induce a retro-Diels–Alder reaction of the adducts (8) formed from hexamethylbicyclo[2.2.0]hexa-2,5-diene and 3-nitrosobut-3-en-2-one were also unsuccessful." @default.
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- W2059639734 date "1983-01-01" @default.
- W2059639734 modified "2023-10-09" @default.
- W2059639734 title "Investigation of the retro-Diels–Alder reaction as a method for the generation of nitroso-olefins" @default.
- W2059639734 doi "https://doi.org/10.1039/p19830001479" @default.
- W2059639734 hasPublicationYear "1983" @default.
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