THE PHOSPHATE-PHOSPHONATE AND PHOSPHONATE-PHOSPHATE REARRANGEMENTS AND THEIR APPLICATIONS-7 [1]: USE OF t-BUTYL AS …

F Hammerschmidt, S Schmidt

Index: Hammerschmidt, Friedrich; Schmidt, Susanne Phosphorus, Sulfur and Silicon and Related Elements, 2001 , vol. 174, p. 101 - 118

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Citation Number: 17

Abstract

Abstract The regioselectivity of metallation of hexyl diisopropyl phosphate (1) depends on the solvent, the temperature, and the base used. The best results are obtained with s- BuLi/TMEDA in hexane and diethyl ether at-78° C. the CH2O group being deprotonated preferentially over the CHO group (3: 1 versus 2, 5: 1). The intermediate phosphonyloxy- substituted alkyllithiums (±)-4 and (±)-5 rearrange to phosphonates (±)-6 and (±)-7, ...

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