Synthesis p. 949 - 952 (1994)
Update date:2022-07-28
Topics:
Ludley
Breitmaier
(E)- and (Z)-2-(p-Formylstyryl)-3-phenylbicyclo[2.2.1]hepta-2,5-dienes (7a,b) are prepared by Wittig alkenylation of 4-(1,3-dioxolan-2-yl)benzyltriphenylphosphonium bromide (4) and 3-phenylbicyclo[2.2.1]hepta-2,5-diene-2-carbaldehyde (5) in tetrahydrofuran to give (E)- and (Z)-2-[p-(1,3-dioxolan-2-yl)styryl]-3-phenylbicyclo[2.2.1]hept a-2,5-di ene (6a,b) in 99% yield (E/Z-ratio 64:36) and the aldehydes 7a,b, after subsequent deprotection. Reaction of the aldehyde 7a with 3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrrylmethane (8) affords porphyrine 1a in 60% yield, reactions of aldehydes 7a,b with pyrrole 9 give porphyrins 2a,b in 39 and 11% yield, respectively.
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Doi:10.1002/hlca.19670500423
(1967)Doi:10.1021/ja01145a117
(1951)Doi:10.1021/jo00105a044
(1994)Doi:10.1021/jm500146g
(2014)Doi:10.1149/2.0241811jes
(2018)Doi:10.1039/C29700001029
(1970)
