Tetrahedron

The regioselective generation of arynes from polyhalogenobenzenes. An improved synthesis of syn-and anti-1, 4, 5, 8, 9, 12-hexahydro-1, 4: 5, 8: 9, 12- …

…, FH Kohnke, F Cardullo, U Girreser, JF Stoddart

Index: Raymo, Francisco; Kohnke, Franz H.; Cardullo, Francesca; Girreser, Ulrich; Fraser Stoddart Tetrahedron, 1992 , vol. 48, # 33 p. 6827 - 6838

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Citation Number: 17

Abstract

The halogenated benzenes, 1, 2, 4, 5-tetrabromobenzene 6, hexabromobenzene 9, p- dichlorotetrabromobenzene 11, and 1, 2-dibromo-4, 5-dichlorobenzene 12, were investigated as 1, 3-bis-, 1, 4-bis-, and 1, 3, 5-tris-aryne precursors by using alkyllithiums and alkali metal amides as the metalating reagents. The arynes were trapped in Diels-Alder reactions with furan as the diene. The title compounds 3a/b are now readily available in ...