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Molecules 2001, 6(3), 194-202; doi:10.3390/60300194
Article

7-(1-Acetoxymethylidene)Benzonorbornadiene: A Versatile Reagent for the Synthesis of 7-Formyl and 7-Hydroxymethyl Benzonorbornadienes

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Received: 30 November 2000 / Revised: 16 January 2001 / Accepted: 16 January 2001 / Published: 28 February 2001
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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.
Keywords: Benzyne; cycloaddition; enolacetates; fulvenes; benzonorbornadienes Benzyne; cycloaddition; enolacetates; fulvenes; benzonorbornadienes
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Warrener, R.N.; Collin, G.J.; Foley, P.J. 7-(1-Acetoxymethylidene)Benzonorbornadiene: A Versatile Reagent for the Synthesis of 7-Formyl and 7-Hydroxymethyl Benzonorbornadienes. Molecules 2001, 6, 194-202.

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