Treatment of 3,4-dihydro-2H-pyran 1 with various alcohols 2 - 10 furnished the tetrahydropyranyl ethers 11 - 19 in the presence of 5M lithium perchlorate in diethyl ether (5M LPDE), which is essentially a neutral medium.

Boga Sobhana Babu

Kalapattukuppuswamy Kuppuswamy B. Balasubramanian

alcohol

ether derivative

lithium derivative

perchlorate

pyran derivative

article

carbon nuclear magnetic resonance

catalysis

catalyst

chemical reaction

chemical structure

proton nuclear magnetic resonance

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Mild and efficient tetrahydropyranylation of alcohols-catalysis by lithium perchlorate in diethyl ether

Tetrahedron Letters

Journal of Organic Chemistry

Chemo- and regioselective conversion of epoxides to carbonyl compounds in 5 M lithium perchlorate-diethyl ether medium

Aldehydes and acetals were very efficiently converted to acyclic and cyclic dithioacetals in 5 M lithium perchlorate/diethyl ether (LPDE) medium at ambient temperature in high yields. Spectroscopic and other experimental evidences strongly suggest the formation of oxocarbenium ion intermediates from acetals in 5 M LPDE which subsequently reacted with thiols to give the dithioacetals. Under the same conditions ketones and their acetals also reacted, albeit very slowly compared to aldehydes and acetals, to yield dithioacetals. The difference in their reactivity was successfully employed in the chemoselective dithioacetalization of aldehydes and acetals in the presence of ketones and their acetals. The chemoselective dithioacetalization of keto aldehydes has been realized with the keto group remaining intact. The present method offers a convenient, efficient, and neutral medium for the deprotection of acetals to aldehydes and also the chemoselective protection of aldehydes to dithioacetals. © 1994, American Chemical Society. All rights reserved.

Chemoselective Protection of Aldehydes as Dithioacetals in Lithium Perchlorate-Diethyl Ether Medium. Evidence for the Formation of Oxocarbenium Ion Intermediate from Acetals

Encyclopedia of Reagents for Organic Synthesis

Protective Groups in Organic Synthesis

Stereo- and regioselective metal salt-catalyzed alkynylation of 1,2-epoxides

Journal	Data powered by TypesetTetrahedron Letters
Publisher	Data powered by TypesetElsevier Ltd
ISSN	00404039
Open Access	No