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Allyl-t-butylmethylsilyl groups were shown to function as alcohol protecting groups whose hydrolytic stability was greater than t-butyldimethylsilyl (TBS) and Si(SiMe 3 ) 3 (sisyl) groups. Pseudo-first-order rate constants for the acidic hydrolysis of primary, benzylic, and secondary allyl-t-butylmethylsilyl ethers in AcOD/THF-d 8 /D 2 O were determined to be 2.94x10...
The tris(trimethylsilyl)silyl (sisyl) group is a photolabile protecting group for primary and secondary alcohols. Sisyl (tris(trimethylsilyl)silyl) ethers 2b-11b of a number of primary and secondary alcohols 2a-11a were prepared in yields ranging from 70-97%. The resulting silyl ethers were stable to aqueous bases, Grignard reagents and Wittig reagents as would be expected for bulky alkoxysilanes...
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