Minimization of Side Reactions during Acidolysis

FIGURE 6.29 Carbenium ions are less reactive if the charged atom is hindered and the molecule can tautomerize to a more hindered form. (A) cyclohexyl, (B) dimethylpentyl (see ref. 132). 

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A Mehta, R Jaouhari, TJ Benson, KT Douglas. Improved efficiency and selectivity in peptide synthesis use of triethylsilane as a carbocation scavenger in deprotection of t-butyl and t-butoxycarbonyl-protected sites. Tetrahedron Lett 33, 5441, 1992. 

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