38624-38-3Relevant academic research and scientific papers
3-chloropropyl and 4-chlorobutyl phenyl ethers as sources of 1,3-dilithiopropane and 1,4-dilithiobutane: Sequential reaction with carbonyl compounds
Foubelo, Francisco,Saleh, Sadiq A.,Yus, Miguel
, p. 3478 - 3483 (2007/10/03)
The reaction of 3-chloropropyl and 4-chlorobutyl phenyl ethers (1) with lithium powder and a catalytic amount of DTBB (5% molar) in THF at - 78 °C followed by successive treatment with a carbonyl compound [R1R2CO = ButCHO, Me2CO, (CH2)5CO, (-)-menthone] at -78 to 20 °C and, after 1.5 h at this temperature, with a second one [R3R4CO = Bu1CHO, PhCHO, Me2CO, MeCOPrn, (CH2)5CO, (-)-menthone] at -78 °C leads, after hydrolysis with water, to the corresponding 1,5-and 1,6-diols (2). Because of the competition of two different reductive cleavages, 1,4- and 1,5-diols 3 were also obtained as side-reaction products.
