Journal article
Alkoxyallylsilanes: Functional Protecting Groups
Abstract
Allyl-t-butylmethylsilyl groups were shown to function as alcohol protecting groups whose hydrolytic stability was greater than t-butyldimethylsilyl (TBS) and Si(SiMe3)3 (sisyl) groups. Pseudo-first-order rate constants for the acidic hydrolysis of primary, benzylic, and secondary allyl-t-butylmethylsilyl ethers in AcOD/THF-d8/D2O were determined to be 2.94×10−3, 8.26×10−4, and 8.26×10−4s−1, respectively. The regioselectivity of acidic …
Authors
Balduzzi S; Brook MA
Journal
Tetrahedron, Vol. 56, No. 12, pp. 1617–1622
Publisher
Elsevier
Publication Date
March 2000
DOI
10.1016/s0040-4020(99)01062-5
ISSN
0040-4020