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Molecules 2001
7-(1-Acetoxymethylidene)Benzonorbornadiene: A Versatile Reagent for the Synthesis of 7-Formyl and 7-Hydroxymethyl BenzonorbornadienesDOI: 10.3390/60300194 Keywords: Benzyne, cycloaddition, enolacetates, fulvenes, benzonorbornadienes Abstract: 7-(1-Acetoxymethylidene)benzonorbornadiene 3, prepared in one step by the addition of benzyne to 6-acetoxyfulvene 2, is hydrolysed in acid solution to form a 3:2-epimeric mixture of syn- and anti- 7-formylbenzonorbornadienes 4 and 5, respectively; the corresponding 7-hydroxymethylbenzonorbornadienes 6 and 9 were produced by reduction of the formyl isomers with sodium borohydride.
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