A. Guijarro, M. Yus
1994
Citations
0
Influential Citations
19
Citations
Journal
Tetrahedron
Abstract
Abstract The reaction of ( Z ) or ( E )-1,4-dichlorobut-2-ene ( 1 , 2 ), or 3,4-diclorobut-1-ene ( 3 ) with an excess of lithium powder and a catalytic amount of 4,4′-di- tert -butylbiphenyl (5 mol %) in the presence of an electrophile [(CH 2 ) 4 CO, Bu t CHO, Me 3 SiCl] in THF at O°C yields, after hydrolysis, the corresponding 1,4- and 1,2-disubstituted compounds ( Z/E )- 4 and 5 , the ratio of them being independent on the starting material. In the case of compounds 4 the Z -diastereomer is largely the major one. When dichlorodiethylsilane was used as electrophile the corresponding substituted silacyclopentene 6 was the only reaction product isolated. A possible mechanism involving dilithiated species is proposed.