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Published on: April 4, 2014
3-Chloropropyl and 4-chlorobutyl phenyl ethers as sources of 1, 3-dilithiopropane and 1,4-dilithiobutane: sequential
1Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain.
Abstract:
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 degrees C followed by successive treatment with a carbonyl compound [R(1)R(2)CO = Bu(t)CHO, Me(2)CO, (CH(2))(5)CO, (-)-menthone] at -78 to 20 degrees C and, after 1.5 h at this temperature, with a second one [R(3)R(4)CO = Bu(t)CHO, PhCHO, Me(2)CO, MeCOPr(n), (CH(2))(5)CO, (-)-menthone] at -78 degrees 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.
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