TY - JOUR
T1 - 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-triepoxytriphenylene
AU - Raymo, Françisco
AU - Kohnke, Franz H.
AU - Cardullo, Francesca
AU - Girreser, Ulrich
AU - Stoddart, J. Fraser
PY - 1992
Y1 - 1992
N2 - 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 two steps in 7% overall yield from 1,2,4,5-tetrabromobenzene 6.
AB - 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 two steps in 7% overall yield from 1,2,4,5-tetrabromobenzene 6.
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U2 - 10.1016/S0040-4020(01)89874-4
DO - 10.1016/S0040-4020(01)89874-4
M3 - Article
AN - SCOPUS:0026649394
SN - 0040-4020
VL - 48
SP - 6827
EP - 6838
JO - Tetrahedron
JF - Tetrahedron
IS - 33
ER -