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Dicyclopropylmethanol is used as protecting group reagent for carboxylic acids; the formed esters are very mildly and selectively cleaved.
Esters of this alcohol undergo extremely rapid solvolysis under mildly acidic conditions such as 1% TFA in dichloromethane. This is due to the effective stabilization of a cation ɑAlpha/D to the cyclopropyl group. Carpino has shown that the dicyclopropylmethyl (Dcpm) group is therefore a potentially very useful, low molecular weight protecting group for the carboxyl function, particularly in peptide synthesis; selective removal in the presence of such acid-sensitive groups as t-butyl, N-Trt, etc. can be achieved: J. Org. Chem., 60, 7718 (1995). See Appendix 6.