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2005
Cycloaddition reactions
O 0070
Broensted Acid TfOH-Mediated Reactions of Methylenecyclopropanes with
— Methylenecyclopropanes (I) and (VII) undergo an unexpected [3 + 2] cy18- 033 Nitriles.
cloaddition reaction with nitriles (II) and (V) in the presence of the strong Broensted
acid TfOH. Side products are the products of Ritter reaction, e.g. (IV), which are obtained in low amounts only. The presence of two substituents at the methylene chain is
necessary whereby at least one substituent must be aromatic. Unsymmetrically substituted methylenecyclopropanes provide the adducts as mixtures of E/Z-isomers with
predominance of the former. — (HUANG, J.-W.; SHI*, M.; Synlett 2004, 13,
2343-2346; State Key Lab. Organomet. Chem., Shanghai Inst. Org. Chem., Chin.
Acad. Sci., Shanghai 200032, Peop. Rep. China; Eng.) — Mischke
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