Chemistry of beta-functionalized alpha-nitroso ethylenes. Methyl beta-nitroso acrylate as heterodienophile in
[formula: see text] beta-Functionalized nitroso alkene 2, obtained from methyl beta-nitropropionate 1 and N,O-bis(trimethylsilyl)acetamide, can function as a good heterodienophile in Diels-Alder reactions. Therefore, 2 was trapped by cyclic dienes to give adducts 4 with the corresponding stereoselectivity. Cycloadduct 4a undergoes retro-[4 + 2]-cycloaddition at 33 degrees C in solution; thus 4a can be used to generate nitroso alkene 2 in neutral medium. Cyclopentadiene reacts with adduct 4a according to an endo-(4 + 2]-cycloaddition scheme to give cycloadduct 5 in low yield.
Tishkov
AA
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
Lyapkalo
IM
Ioffe
SL
Strelenko
YA
Tartakovsky
VA