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Paper | Regular issue | Vol 31, No. 5, 1990, pp.889-893
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5358
The C-O Bond Cleavage of Cyclic Ethers with Tris(phenylseleno)borane-Lewis Acid

Tadashi Kataoka, Mitsuhiro Yoshimatsu, Hiroshi Shimizu, Yoshitaka Kawase, and Mikio Hori*

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

Tris(phenylseleno)borane (1) has a hard boron element and a soft selenium element, and therefore it was expected that 1 cleaves the C-O bond. Tetrahydrofuran and tetrahydropyran were cleaved with 1 in the presence of zinc iodide to produce the δ- and ε-phenylseleno alcohols (7 and 8). The C(5)-O bond of 2-methyltetrahydrofuran (5) was regioselectively cleaved with 1 and a catalytic amount of tin(IV) chloride to afford the δ-phenylseleno alcohol (12). The selenoborane (1) was a weak reagent for the C-O bond-cleavage and cleaved only cyclic ethers selectively.