Abstract
Abstract The t-butyldimethylsilyl (TBDMS) protection1–3 of alcoholic and phenolic hydroxy groups has attained much importance of late. Certain shortcomings, however, of this protective method have recently come to light. These include acyl migration4 during the fluoride anion mediated desilylation of acylated/silylated glycerols, and cleavage of TBDMS groups under catalytic hydrogenation conditions intended for benzyl ether cleavage4. Further, aryl anions of trimethylsilyl protected phenols have been shown5 to rearrange into o-trimethylsilyl-phenolates; similar reaction of a TBDMS protected phenol has been observed6 in this laboratory. The more labile trimethylsilyloxy group has also been reported7 to act as a leaving group, if present at an allylic or benzylic site, towards a variety of nucleophiles (H−, alkyl Grignards, malonate anion). However, benzyl TBDMS ether is stable towards ethylmagnesiumbromide under reflux6.
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