F. Foubelo et M. Yus, 3-chloropropyl phenyl ether as a 1,3-dilithiopropane source: Sequential reaction with carbonyl compounds, TETRAHEDR L, 40(4), 1999, pp. 743-746
The reaction of 3-chloropropyl phenyl ether (1) with lithium powder and a c
atalytic amount of DTBB (2.5% molar) in THF at -78 degrees C followed by su
ccessive treatment with a carbonyl compound [E-1 = (BuCHO)-C-t, Me2CO, (CH2
)(5)CO] at -78 to 20 degrees C and, after 1 h at this temperature, a second
one [E-2 = (BuCHO)-C-t, PhCHO, MeCOPrn, (CH2)(5)CO] at -78 degrees C leads
, after hydrolysis with water, to the formation of the corresponding 1,5-di
ols (2), in which two different electrophilic fragments have been introduce
d. (C) 1999 Elsevier Science Ltd. All rights reserved.