Synthesis and Photocleavage of Quinoline Methyl Ethers: A Mild and Efficient Method for the Selective Protection and Deprotection of the Alcohol Functionality*
Anthony A. Provatas A C , Gary A. Epling B and James D. Stuart AA Center for Environmental Sciences and Engineering, University of Connecticut, Building 4 Annex, 3107 Horsebarn Hill Road, Unit 4210 Storrs, CT 06269-4210, USA.
B Deceased (9 September 2001). Formerly of University of Connecticut, USA.
C Corresponding author. Email: anthony.provatas@uconn.edu
Australian Journal of Chemistry 69(7) 763-769 https://doi.org/10.1071/CH15627
Submitted: 7 October 2015 Accepted: 9 December 2015 Published: 18 January 2016
Abstract
The synthesis and photocleavage of quinolinyl methyl ether-protected alcohols is reported in this study. A variety of quinoline methyl chlorides were synthesized, and protection of the various alcohols was performed via a substitution reaction in the presence of a strong base. Photocleavage of the quinolinyl methyl ether moiety proceeded under visible light with the formation of the charged quinolinyl radical intermediate through a single-electron transfer in the presence of a photosensitizer dye leading to the deprotected alcohol in excellent yields. The utility of triethylamine as a sacrificial reductant and d-sorbitol as a radical scavenger were also investigated in this study.
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