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Alkoxyallylsilanes: Functional Protecting Groups

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
56
Issue
12
Identifiers
DOI: 10.1016/s0040-4020(99)01062-5
Keywords
  • Hydrolysis
  • Kinetics
  • Protecting Groups
  • Silicon And Compounds

Abstract

Abstract 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 2O were determined to be 2.94×10 −3, 8.26×10 −4, and 8.26×10 −4 s −1, respectively. The regioselectivity of acidic hydrolysis of allylbenzyloxy- t-butylmethylsilane 1 was examined under strong acid ( p-TsOH/CD 2Cl 2) and weak acid (AcOD/THF- d 8/D 2O) conditions. In both cases, benzyl alcohol was initially produced exclusively from silicon–oxygen bond cleavage: allylic cleavage was only subsequently observed over time. However, the allyl group of the silyl ether could be hydrosilylated. The resulting alkoxy-functionalized disiloxane had greater hydrolytic stability under acidic conditions than the starting alkoxyallyl- t-butylmethylsilane.

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