3-Chloropropyl phenyl ether as a 1,3-dilithiopropane source: Sequential reaction with carbonyl compounds

Article abstract of DOI:10.1016/S0040-4039(98)02360-0

The reaction of 3-chloropropyl phenyl ether(1) with lithium powder and a catalytic amount of DTBB (2.5% molar) in THF at -78°C followed by successive treatment with a carbonyl compound [E¹ = Bu(t)CHO, Me₂CO, (CH₂)₅CO] at - 78 to 20°C and, after 1 hat this temperature, a second one [E(2) = Bu(t)CHO, PhCHO, MeCOPr(n), (CH₂)₅CO] at -78°C leads, after hydrolysis with water, to the formation of the corresponding 1,5-diols (2), in which two different electrophilic fragments have been introduced.