A. Guijarro, M. Yus
1994
Citations
0
Influential Citations
17
Citations
Journal
Tetrahedron
Abstract
Abstract The reaction of 1,3-dichloropropene (1, ca 1/1 Z/E mixture) with an excess of lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5 mol %) in the presence of an electrophile [Me2CO, Et2CO, (CH2)4CO, (CH2)5CO, ButCHO, Me3SiCl] in THF at O°C affords, after hydrolysis with water, the expected unsaturated 1,5-diols 3 as a Z/E mixture or disilane (E)-4. Treatment of isolated compounds (Z)-3 with 85% phosphoric acid gives the expected dihydropyrans 5.