Hydroxyl Protection. III. Synthesis and Cleavage of 2-(Phenylseleno)Ethyl Ethers
- 1 January 1975
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 5 (5) , 367-368
- https://doi.org/10.1080/00397917508062091
Abstract
During a quest of new hydroxyl-protecting groups, our attention was focused at one time on the 2-(phenylseleno)ethyl residue. It has been established that selenides are responsive to oxidation by H2 O 2,2 O 3,3IO4,4etc., to afford selenoxides; aryl alkyl selenoxides undergo facile thermal decomposition5 at room temperature or below. Thus starting from 2-(phenylseleno)ethyl ethers (1), the reaction sequence would lead to vinyl ethers and PhSeOH via the intermediates (2). As vinyl ethers are easily hydrolyzed on contact with mineral acids to acetaldehyde and alcohols, the value of the PhSeCH2CH2 group for blocking hydroxyl becomes clear.Keywords
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