Tetrahedron

Rapid atropisomerization of 1, 1′: 5′, 1 ″-ternaphthalene-2, 2′, 6′, 2 ″-tetrol (TERNOL) and its inhibition by tethering at positions 7 and 7 ″

T Sugimura, N Matsushita, K Minokami, S Kurita

Index: Sugimura, Takashi; Matsushita, Naohiro; Minokami, Keiko; Kurita, Shinya Tetrahedron, 2007 , vol. 63, # 8 p. 1762 - 1769

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Citation Number: 7

Abstract

Atropisomerization of 1, 1′: 5′, 1 ″-ternaphthalene-2, 2′, 6′, 2 ″-tetrol (TERNOL) is very fast under basic conditions. The stereochemical instability is attributed to the nature of oxide anion of the central 2, 6-naphthodiol moiety. Ring-closing metathesis of 7, 7 ″- diallyloxy TERNOL results in intramolecular tethering in a high yield, which intrinsically inhibits the rapid isomerization. Bidentate sites in the tethered TERNOL are proved to ...