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2005
Ring opening reactions
O 0132
Broensted Acid Mediated Ring-Opening Reactions of Methylenecyclopropanes: A
Counter Ion Effect. — In the presence of equimolar amounts of water and
14- 043 Dramatic
catalytic amounts of Broensted acid C8F17SO3H methylenecyclopropanes (I) undergo
ring opening/etherification reactions to give homoallylic ethers (II). In contrast, by use
of stoichiometric amounts of TosOH as Broensted acid the cyclopropane ring is opened
directly to afford sulfonated homoallylic alcohols like (V). In the case of unsymmetric
cyclopropanes, the corresponding ethers (II) are formed as single isomers, whereas ring
opening by TosOH gives mixtures of E/Z-isomers. — (SHAO, L.-X.; HUANG, J.-W.;
SHI*, M.; Tetrahedron 60 (2004) 51, 11895-11901; State Key Lab. Organomet.
Chem., Shanghai Inst. Org. Chem., Chin. Acad. Sci., Shanghai 200032, Peop. Rep.
China; Eng.) — Klein
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