Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
In-situ generated nitroso alkenes underwent smooth hetero Diels-Alder reactions with E-1-[N,N-bis(trimethylsilyl)amino]-1-propene (1) and furnished 1,2-oxazines 7-9 in good yields. In contrast, the other n-disilylated enamines Z-1, 2, and 3 did not react with α nitrosostyrene. Thus, a very simple kinetic separation of E/Z-1 is possible. By addition of dichlorocarbene olefin E-1 could also be converted into the corresponding dichlorocyclopropane 14. The reactivity of 1 is compared to that of other electron-rich olefins, and it is discussed regarding NMR data, photoelectron spectra as well as AM1-calculations.
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