TY - JOUR
T1 - A new route to phenanthrene derivatives
AU - Giuffrida, Daniele
AU - Kohnke, Franz H.
AU - Parisi, Melchiorre
AU - Raymo, Françisco M.
AU - Stoddart, J. Fraser
PY - 1994/7/4
Y1 - 1994/7/4
N2 - 4,5-Dimethylbenzo[1,2-c:3,4-c′]difuran (7) is a highly reactive bisdiene, which undergoes Diels-Alder reactions with a wide variety of dienophiles, including dimethyl acetylenedicarboxylate and cis-1,4-dichlorobut-2-ene, to give phenanthrene derivatives, e.g. 10 and 12, respectively, following (hydrogenation and) dehydration of the bisadducts 8 and 11, respectively. 9,10-Dimethyl-1,4:5,8-diepoxy-1,4,5,8-tetrahydro-phenanthrene (5), as a result of thermal decomposition of either (i) its bisadduct 6 with tetraphenylcyclopenta-dienone or (ii) its hydrogenated derivative 14, is a very convenient precursor of 7.
AB - 4,5-Dimethylbenzo[1,2-c:3,4-c′]difuran (7) is a highly reactive bisdiene, which undergoes Diels-Alder reactions with a wide variety of dienophiles, including dimethyl acetylenedicarboxylate and cis-1,4-dichlorobut-2-ene, to give phenanthrene derivatives, e.g. 10 and 12, respectively, following (hydrogenation and) dehydration of the bisadducts 8 and 11, respectively. 9,10-Dimethyl-1,4:5,8-diepoxy-1,4,5,8-tetrahydro-phenanthrene (5), as a result of thermal decomposition of either (i) its bisadduct 6 with tetraphenylcyclopenta-dienone or (ii) its hydrogenated derivative 14, is a very convenient precursor of 7.
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U2 - 10.1016/S0040-4039(00)76982-6
DO - 10.1016/S0040-4039(00)76982-6
M3 - Article
AN - SCOPUS:0028332496
SN - 0040-4039
VL - 35
SP - 4839
EP - 4842
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 27
ER -