A 1,3-sp(2),sp(3)-hybridized dilithio intermediate by direct lithiation of cyclopropylidene diphenylmethane

作者：Lillo Victor J; Gomez Cecilia; Yus Miguel^*

来源：ARKIVOC, 2010, 29-44.

• Lithium
• naphthalene
• alkylidene cyclopropane
• ring opening
• electrophilic substitution
• diols

The reaction of cyclopropylidene diphenylmethane 1 with an excess of lithium and a catalytic amount of naphthalene (5 mol %) at -20 degrees C, followed by addition of an electrophile [E = H2O, D2O, t-BuCHO, Me2CO, Et2CO, n-Pr2CO, i-Pr2CO, (c-C3H5)(2)CO, (CH2)(5)CO] at -78 degrees C and final hydrolysis with water at -78 degrees C to rt gives the corresponding products 5, which in some case are contaminated with the corresponding by-products 6, resulting from the incorporation of only one electrophilic moiety at the intermediate dianion of type 2. The separation of both reaction products is easy by simple column chromatography.

• 出版日期2010